Try Thinking of Strategic Planning Like Sailing

“We cannot direct the wind, but we can adjust the sails” – Dolly Parton


Here on the New England coast, I’ve sailed my whole life. So whenever I’m looking for a fitting analogy to explain how important strategic planning is, I inevitably think of the adventures and mishaps that can come with sailing.


One weekend when I was a kid, we set sail for Block Island, a beautiful island off the coast of Rhode Island. We planned to take the journey in two legs, anchoring in Newport for the night. It started out as the perfect day with the winds on our beam, and we quickly cruised along. 


The chill vibe didn’t last long. Lacking the weather apps we have today, we were unprepared for a squall that came up, bringing high winds and lightning. Instead of arriving in Newport, we were forced to pull into a shelter harbor to regroup. 


The next day, as we headed out from the bay into the open ocean, the wind was directly in front of us. This meant we had to tack the entire time, which is basically like zigzagging your way to your destination. Three hours later than planned, we motored into New Harbor on Block Island- exhausted and excited.


Sailing is basically a crash course in why strategic planning at your company is so important. It’s not hard to say what sunny destination you want to arrive at. But how often are you pausing to regroup and take stock of where you are compared to the course you set?


In sailing, any number of factors can affect your progress: the winds, the tide, the weather, the odd lobster pot that wraps around your rudder (especially when the job of watching out for pots is given to an 8 year old). We make regular adjustments- big and small- to respond to the unexpected.  


So too in your company: talent gaps, external competition, proper estimation, crucial activities not being prioritized- can affect whether or not you make it to your destination. If you’re not periodically pausing to assess where you are, you may eventually find yourself wildly off course, unsure of how you got there.


So avoid putting off your next strategy session because the day-to-day feels more pressing. When you regularly reflect on how far you’ve come and where you need to go next, you’ll be in the best long-term position to succeed. In my next article, I’ll share the key questions to ask in your strategy session.


This is Part 1 of a strategic planning series. Stay tuned for the key questions to ask in your next strategy session.

How Founders Can Defeat Self-Doubt For Good

A founder I coach reached out to me with an all-too-common pain point. A negative comment on her company Facebook page sent her into a tailspin–not only wasting a workday, but consuming her with self-doubt.


While the occasional negative Facebook critique may be inevitable, the accompanying self-doubt doesn’t have to be.


Here are the transformative beliefs I share with  founders in a similar situation:


Concept #1: Your feelings are created by your thoughts which alter how you experience a given event.


According to cognitive psychologists, our thoughts create our moods- like self-doubt, anger and depression. In Feeling Good, David Burns explains that our brain takes in an “event” and we interpret that event as a “thought.” The thought triggers in us certain “feelings” and our “actions” follow.


Here’s a look at how the process works:



Let’s apply this to the situation with the founder I referenced above– I’ll call her Jane. Jane read the negative Facebook post (the “event”) and thought, “this proves I have no idea how to run this business”. As a result, she felt overwhelmed and anxious. She then spent an unproductive evening questioning whether she had what it takes to be successful. 


Jane saw the Facebook post as causing her bad night. But that’s not the full story. She may not have been able to control the critical comment, but she did have power over the downhill spiral that she subsequently went through.  


Concept #2: An event doesn’t always result in the same thoughts, which proves that the downward spiral is not as inevitable as it might seem in the moment. 


An event may trigger irritated thoughts in us one day, and yet the same situation barely hits our radar the next. 


A few months ago, a team member approached another founder I work with, who I’ll call Tim, requesting more responsibility and a big raise. He immediately thought, “this employee is so entitled”. He then spent the next hour feeling irritated and complaining to his co-founder.


However, when a different employee reached out to Tim and made a similar request the following week, his reaction was more measured and open-minded.  


Even though it was basically the same situation, he had totally different thoughts, leading to different feelings and actions. Since an event can cause multiple thoughts, we therefore have more freedom over our feelings than we often believe. 


Concept #3: Our negative thoughts are almost always fueled by irrational or inaccurate thoughts. 


Irrational or inaccurate thoughts- also known as distorted thoughts- don’t serve a positive or constructive purpose in achieving our long term goals. Cognitive psychologists share many types, but here are some that I frequently see:


“All-or-nothing thinking” is where we view things in black and white categories. Jane did this when she read one critical comment and immediately concluded that she wasn’t good enough. 


“Labeling” is an extreme form of overgeneralization, which Tim was doing when he thought of his employee as “entitled.” Labeling the employee may have felt cathartic in the moment, but probably didn’t reflect the full picture.


“Disqualifying the positive” is when we refuse to acknowledge anything positive about a person or situation. Two co-founders I’m working with have been struggling with their partnership. They’re solely focusing on their negative beliefs about the other. This helps them each feel “right”, and it’s making it impossible for them to view their partnership with mutual purpose.   


Concept #4: Be aware of the thoughts that benefit you, and re-write the ones that don’t. 


The thoughts that benefit you serve a constructive purpose in your life. They help you achieve your true goals. They help you accurately problem-solve and process the world around you, without negatively affecting your or others’ self-esteem.


Thoughts that don’t benefit us- like those that trigger self-doubt- get in our way. The first step to addressing it is to recognize the way in which it’s inaccurate or irrational. Then, we challenge the thought by rewriting it. 


Jane rewrote her “I’m not good enough” all-or-nothing thought with, “even though this customer’s criticism is valid, it doesn’t mean there’s anything fundamentally wrong with me or my company. I’m sure my team can figure this out.”


Tim rewrote his “this employee is so entitled” labeling thought to “our views on this are totally different. Why might he think he’s ready for more responsibility and money?”


And the co-founders are challenging their negative beliefs about each other by asking themselves: “Is it really true that the other person brings nothing to this partnership? What’s at least one valuable thing they add to this company?”




Self-doubt is the ultimate saboteur, chipping away at our confidence and our highest aspirations. It’s an unproductive emotion that most of us have experienced at some point in our lives. 


What’s more, these distorted thoughts can destroy our dreams and our goals if left unchecked. 


Learning these tools will take consistent practice, but the payoff will be priceless. 


How To Be A Good Boss During An Unsettled Time

As a leader who cares about your people, one of your goals in unprecedented times, is to be a good boss; in other words, to guide your team and help them stay focused.


And intentions matter– though, they are not enough on their own as the best intentions can go sideways. For example, I was on a team where the leadership called for a daylong retreat after the 2016 presidential election. It was terrible timing. The day was hyper-scheduled and no one had any personal space to process their feelings. So, first things first, avoid scheduling intense meetings when there’s a good chance that the team’s collective mindshare will be elsewhere.


And what if the outside distraction is happening not for just one day, but an extended period (like we’re experiencing right now)? Here’s how to navigate through it and keep your team on track:


Advice #1: Treat Your Team Members as Individuals


Each of your team members likely has different opinions about a given event. Moreover, people process their feelings in different ways. One person might need to offload their personal thoughts before getting their head back into their work, while another might prefer to process things privately. Some may enjoy openly debating the day’s events, while others feel it’s too personal.


Make space for these differences by getting to know your team member’s preferences and letting them take the lead on how (or whether) they engage on topics that aren’t core to the work. 


And avoid the temptation to lead off with your own opinions, as your status will naturally influence the discussion.


Advice #2: Be A Unifier 


When your team is struggling with conflicting emotions and opinions, help them focus on what they share in common. Start by setting your personal beliefs aside; it’s hard to unify a team when you’ve taken a strong position on a topic. 


To be clear: there will be times when you deliberately use your voice to communicate what you and your company stand for, leaving no room for gray areas. Assuming this isn’t one of those times, then opt to keep your voice as neutral as possible. 


Do your best to be a calm and stable presence. Strive to create an environment that makes everyone feel included. The more polarized your team is, the more centered you have to be.      


Next, drive their attention toward your common purpose as a team. Connect back to your Core Values to remind your team of the beliefs and behaviors that you all share. Push them to get beyond the external distraction by reengaging in their work. They may even find it motivating to re-focus on something within their control.


Advice #3: Offer extra support 


Create opportunities for people to set aside the negativity and make a positive connection with each other on a human level. Break up the normal workday and schedule an energy-boosting Mystery Call. It’ll improve the team’s vibe and build culture. And for individuals, the Headspace podcast offers some grounding perspective. 


And if folks start to seem overwhelmed, encourage them to take time off to decompress and relieve stress. (Pro tip: this is where your company philosophy on time off and flexibility will be put to the test). Even a few hours off can be a helpful recharge. 


At the same time that your team needs you to steady the ship and keep them focused during unsettled times, you need to fill your cup too. Be sure to lean on the people in your life, and use the extra outlets you offer to your team, to process your personal thoughts and reactions. 


How To Create A Positive Feedback Process For You And Your Team

The first feedback process I was ever a part of also happened to be the best.


I was fresh out of grad school and part of a small team at a big, fast-growing company. We were an innovation lab of sorts; finding creative solutions to traditional HR processes. 


Our little team included a huge diversity of talents, opinions, and backgrounds. And with this being the first “real” job for us all, we were inexperienced in almost every sense. We had few work basics under our belt to help us navigate our work and our issues. But, at the same time, our lack of experience helped us look at everything with fresh eyes. We communicated and debated passionately about everything. 


Despite- or maybe because of- our intense passion and talent, we struggled to get things done. So, when nearly every attempt to make a decision started to feel like we were knocking heads, we figured it was time to take a close look at how we were working together.


We decided to create a feedback process so we could talk about our experiences working together and get to the bottom of our conflict. Our goal was to make the exercise as honest, productive and trust-strengthening as possible.


Creating our own feedback process felt intuitive, however, we later learned that most people use standard templates.


I’m glad we did it our way, because our approach led to open and transparent feedback. And due to its simplicity and results, it’s my favorite process to share with leaders to this day. Here’s how we did it. 


We agreed on a set of open-ended questions. We were ready to be open with ourselves and share candidly with each other. 


Because our goal was to become a higher performing team, we asked ourselves questions like, “To what extent does the other person encourage all points of view to be added to our pool of shared meaning”? “To what extent do they fully back a decision once the team has made it”? “What’s one uniquely valuable strength that I (the feedback giver) experience with this team member”? “What’s one thing I’m struggling with or feel could be improved upon with the way we work together?” 


We responded in writing to the questions for each member of the team. This gave us the space to reflect and provide thoughtful responses. It also ensured a better chance that the feedback would be fully absorbed. 


Moreover,  writing (and reading) the comments first turned out to be a great dress rehearsal for discussing it in person. 


We met with each other individually to discuss. By that point, we had personally processed the feedback so our emotions weren’t raw. Regardless of people’s frustrations heading into the process, each conversation was constructive, respectful and truthful. 


We weren’t looking to create something unique. We simply created what we thought would achieve the level of understanding and alignment we knew we needed.


I later came to learn that few companies communicate this openly: both in general, and when it comes to giving and receiving feedback.


In fact, many feedback systems fall short because the honesty and transparency that’s needed isn’t fully present in their company’s culture. So the things that require more courage- like looking someone in the eye when sharing your thoughts- become an optional step versus being core to the experience. 


1 Communication Secret of Successful Leaders

Even when I’m driving in my car listening to the news, I focus on how leaders share their ideas and opinions. The most effective messages focus on mutual purpose, and the most successful people know this.


As an executive coach and longtime fan of the Crucial Conversations methodology, I regularly study how people communicate. Recently, I heard Dr. Anthony Fauci being interviewed for his latest views on coronavirus. Fauci has become a household name these days as the country’s top infectious disease expert. But, he could also teach a masterclass on how to maintain mutual purpose during critical moments.


Simply put, mutual purpose is the common goal that you share with someone else. Whether we realize it or not in the moment, we’re all constantly working to create (or nurture) mutual purpose with the people in our lives: with our spouses, kids, co-founders, clients and team members. And what differentiates our more successful days is when we’re aware of that in our communication. 


For instance, it feels like a battle to get my kids to eat nutritious foods, but on our better days, we find a balance because we mutually agree that being healthy is important. Likewise,  challenging a client to see where her communication style isn’t serving her could be an uncomfortable conversation, but we share the goal of helping her run her company better. 


Each time I watch him speak, I’m struck by Fauci’s gift for staying focused on shared goals. He rarely, if ever, gets sidetracked by politics, rumors, below-the-belt comments or his own ego. All on top of having little sleep and a crushing schedule; two stressors that make quick work of the rest of us. Instead, he seems to stick to the facts as much as possible, speaking with patience, humility, and positive intent.


This is a guy who is probably under the worst strain of his life. And yet, he seems to be totally devoid of the styles under stress that derail the rest of us during crucial moments. 


Usually when we feel threatened- that is, when our reputation or safety or ego is at stake- we become silent (to protect ourselves) or violent (to win at all costs).   If we become triggered, our original goal gets replaced by a new one: either to protect ourselves or to win. Which means that we’re no longer focusing on the thing we really want, and sabotaging our chances of real success.


Let’s take two co-founders, whose mutual purpose is to successfully launch their product, be hugely profitable and pay back their friends and family’s investment. Things are going pretty smoothly until a serious issue comes up and their plan needs to be refactored. Their launch gets pushed out by six months, diminishing their chance at being first to market. 


Co-founder A, who’s been promising their beta customers that it would be ready next month, is irritated that his reputation will be affected. And his maxed out credit cards remind him daily that failure isn’t an option. He goes violent: verbally attacking the team and controlling communication by cutting people off and dominating the conversation. Co-founder B feels responsible for the screw-up and is starting to dread that his parents invested their savings in this venture. He goes silent; sarcastically responding to comments and withdrawing from the conversation altogether. 


It’s in these crisis moments that I bring co-founders back to their mutual purpose. Their real goal is not to defend themselves, deflect responsibility, or punish others for screwing up; as central as that might feel in the moment. It’s to be the first to market with their incredible product, which requires everyone on their team feeling safe to contribute at the highest possible level. 


The act of pausing counter-productive behaviors and remembering what they both really want resets the brain so that it’s back in control. Finding their way back to their shared goal helps them to assess options and a way forward that wasn’t possible when they were emotionally charged. 


I get excited when I see a skillful communicator like Fauci, because I know how hard it is to be that good. The great news is that being a great communicator can be learned. It takes practice, self-awareness, and celebrating progress over perfection.

2 Questions for Essential Employee Feedback

It’s 2 AM on a Saturday and you’re facing another sleepless night. Things with your company have been moving so fast lately that you feel like you’re losing your handle on it. Come to think of it, you have good reason to feel that way. Your team has gone from five to 20 people in the last year and your culture has morphed into something you barely recognize. And at this new scale, employee feedback isn’t happening as organically as it used to. It’s all starting to feel disconnected. 


If your company is in the process of scaling, or you’re preparing for rapid growth, asking your team two essential questions can help you be deliberate about your people and culture through the process. No one knows what makes your company a meaningful place to work more than your employees. As a result, these questions give a quick and accurate view on how people are feeling, your company’s competitive strengths, and what’s standing in the way of success. 


1) What’s the #1 reason you stay at this company?


Answers to this question reveal what people most value in the context of the rest of their lives. Perhaps it’s being on the ground floor of something truly innovative, or an exceptional team vibe. Or maybe working 100% remote allows them to get their kids off the bus after school. 


2) What would be the #1 thing that would motivate you to leave?

This question gets to the heart of people’s non-negotiables. The things that they love and won’t tolerate a change to, or the fundamental problems that need to be immediately addressed. It’s also a surefire way to learn if an employee doesn’t feel supported, or the company’s protracted growing pains are diminishing confidence, or if someone feels stuck in their job.


Why the questions work


They distill everything down to the essential truth.  Requiring people to pick their #1 reason filters out all the lesser factors that can often cloud your understanding of what’s most important.


They point to highly specific things that matter most to a great work experience. There’s no fluff to these questions, and responses tend to be equally direct. The result is a rich understanding of your people and your company. (Unless, of course, your team is afraid to tell you the truth).


They highlight the greatest threats to people staying and your company’s biggest vulnerabilities. You learn in clear terms what’s at risk if you remove or change their #1 thing. This input will help you plan for the future.   


In my experience, pointed questions lead to pointed answers.  You may be surprised by what actually drives and motivates your people. Above all, this knowledge will allow you to prioritize what’s “nice to have” versus non-negotiable for your culture. 


Introducing Founder Connect

“Honestly, I’m petrified I’m gonna fuck it all up. Please tell me that other people you work with feel this way too.”


That was the start of my first conversation with one of the founders I work with. She had reached out to me at a point when her new Head of Product had abruptly left after just three months, her team had tripled in size in two years and churn was crushing her bottom line. She was overwhelmed, to put it lightly.


Every founder I’ve worked with has shared a version of this sentiment with me during our work together. They want to know that they’re not the only one who feels this way.


Life as a founder can be lonely: The stakes are high and the future is often unknown. 


And while I assure them all that they are, in fact, in very good company, that reassurance helps only a little.


Surprisingly (or, maybe not surprisingly), the endless amounts of content streaming into our inboxes, sharing battle stories of “failures”, adds little reassurance. That’s because “failure” in the startup world is celebrated in the abstract, usually by someone who is now wildly successful. It’s  become such a buzzword that founders who are in the trenches can no longer relate. They’re in the middle of it, living the gritty reality of sleepless nights, wild swings between the highest highs and deep self-doubt, and precarious finances.


I’ve been thinking a lot lately about the contrast between what we read and listen to and what real people experience. Why is it that we only show the sunny side of hard stuff? Why do we talk about the battle only after it’s won? 


As an executive coach with a background in Psychology, I know all the textbook reasons why people don’t talk about the tough stuff when they’re in it. It’s hard enough on our ego and emotional bandwidth to be going through it, never mind narrating it for other people. Our psyche does whatever it can to protect ourselves from feeling any more harm than necessary.


Ironically, this self-protectionism can lead us to feel further alone. What’s more, it can affect how you show up with your team and the people you care most about. It messes with your sleep habits. And it destroys your ability to make good decisions.


But,  when that paradigm changes, the result is nothing short of magical.


Then I came across this conversation between Oprah and Michelle Obama, where they discussed the power of connecting to the “humanness” of our shared experiences. Michelle commented, “We gravitate to one another when we share the best and the worst of ourselves”.


“Exactly” I thought.


What we lack right now in the startup community is a shared experience. 


But what does that look like? 


Think for a minute about a time when you connected- I mean, really connected, with someone about something that you both had in common. On a topic that was really important to you, that you were hugely passionate about. (Hopefully, you’ve had at least a few opportunities to do this with your business. If so, think of one of those examples for this!).


Did that experience or conversation give you new energy to tackle something in a different or better way? Did something that previously felt impossible suddenly feel totally possible? 


That’s the power of real connection. 


So, I’m creating the Founder Connect project to find the answers to the questions that all of my founders are asking–and for all of you out there who wish you could hear from real people who are battling the same real shit that you’re going through.


I’ll be interviewing courageous founders who want to pay it forward and share their wisdom about their proudest moments, lowest points and biggest lessons learned–while they’re in the midst of learning them.


My goal is to explore whether founders face specific common challenges, and what tools and resources they’ve used to respond to them. I’ll ask about the advice they wish they had gotten along the way, and advice they’d share with other founders who are just starting out. By shedding light on individuals’ stories, it is possible to create a more human experience for founders going through their startup journey.


So, here’s my ask: If you’re a founder (or know one who would be great for this project) who’s willing to be real about your personal startup experience, please contact me.  My only asks (in addition to your candor) are that you’ve been in business for more than three years and have more than three members on your team.


And, stay tuned. I’ll be sharing Founder Connect observations and insights along the way, and report my complete findings at the end.


3 Reasons Why Your Team Doesn’t Tell You the Truth When You Need to Hear It Most

Running a company can be thrilling and fulfilling. It can also be humbling and exhausting, especially when things aren’t going well. 


You know those moments: When your team drops the news that the big release is going to be delayed by months– a week before you were supposed to launch. Or when your Head of Growth abruptly announces he’s leaving the company. Or when you and your team need to make a critical decision and the discussion is unproductive or awkward.


What you may not have realized in the midst of these communication gaps is that your team was sending you a message with their silence. They’re choosing not to tell you the truth at critical moments because they’re afraid you won’t listen to (or like) what they have to say. 


It’s incredibly hard for a leader to spot that this is happening in their company. On the surface, folks may be agreeable and upbeat. You might even have the impression that they’re engaged and that everything’s on track. 


But people’s thoughts and opinions are more often like an iceberg. There’s the information that they feel safe sharing with you; the stuff that you see above the surface. And then there’s everything that’s below. 



Too often what remains below the surface are essential truths like, “I know how critical it is that we release next week but our scope and timeline is severely out of whack”, or “I can’t be successful at this company because you micromanage my every move”. Or, “I’d rather deal with awkward silence than have you blow up over my opinion”. 


After you get over your initial frustration, you might wonder: how did this happen?


It could have started when a critical decision needed to be made and people felt their opinions weren’t valued. Or maybe it was a series of less significant moments that added up over time; times when your team felt unheard, or where they witnessed others be subtly (or not-so-subtly) rejected. 


Whatever the case, your team stored those experiences as instruction on how they should behave at your company. If employees believe that conflict and criticism can’t be worked through safely and constructively, or that there will be blowback for disagreeing, they’re more likely to keep differences of opinion below the surface.


This is a silent killer for a startup, where margins are thin and missed releases can’t be afforded. When leaders don’t listen, teams don’t perform to their potential. The impact to the bottom line, customer satisfaction and employee morale is obvious. 


On top of that, you’re hiring people for their expertise and ideas. When folks feel like their value is being wasted, they’re  not likely to stay for long– starting with your best people.


Your mission is to create a culture that encourages as much information above the waterline as possible. And that starts with listening to your people, especially if you don’t like or agree with their opinion.


Below are several common watchouts that you need to avoid- and what to do instead.


#1 You Come Across as Defensive



Years ago my team and I were in the middle of a major software launch that required a ton of new configuration. It wasn’t going well because we were trying to retrofit our processes onto a platform that we were quickly learning wasn’t designed to do what we expected. 


Day after day, my stress and frustration built as I tried to forcefit the app to meet our requirements. I felt myself regularly losing patience: with our vendor, my team and the new software that was less than it was promised to be. I was unhappy with any answer that didn’t align with what I wanted to hear. In retrospect, I was behaving like the worst version of myself.


Thankfully, a teammate I really trust and respect pulled me aside and candidly told me what I was doing to everyone around me. I was shocked to realize that she was right.


In the heat of the moment, I had no idea that my emotions were that obvious, or that I was killing the team’s morale. It definitely wasn’t the kind of leader I wanted to be. I got busy repairing relationships and becoming way more attuned to my behavior. 


Thankfully, a sincere apology and having an understanding team can go a long way. I became much more aware of my actions and behavior, especially in heated moments. Ultimately, I was able to get through it and become a better leader for it.


It’s natural to be attached to our own ideas and decisions, especially when they’re what got us this far. 


As a startup, you’re bringing new people onto the team with broader and deeper expertise. If you hired right, they’ll have their own opinions about how things should be done. They likely won’t appreciate the historical context for why writing the code on Ruby instead of Python was the best option at the time. 


To your sensitive ears, their comments may sound naive or judgmental. The questions might even nag at some of your inner fears. This, in turn, can trigger defensiveness.


To avoid this, watch out for sarcasm, interrupting, or using a sharp or abrupt tone. 


And your body language is just as important as your words. Pay attention to your facial expression and posture. Do you look as annoyed as you feel on the inside? Is your body tense or closed off?


What to Do Instead


Really listen

Turn off your inner dialogue and seek to fully understand what your teammate is telling you, without judgment or reaction. Your body language is the most powerful way to show you’re paying attention and that you respect what the other person is saying. Stay open and just…  listen. Notice what they’re telling you, verbally and non-verbally


Probe before responding

After listening, ask probing questions before giving your own point of view. More information will deepen your understanding and prevent you from making assumptions. It’ll also give you time to formulate a more thoughtful response. “Help me understand what you mean by…” and “I’m curious about….” are great question starters.



#2 You Don’t Like to Be Challenged 


I once had a client who was exceptionally gifted at getting the most out of her team. She knew how to harness the deep expertise of each person, and took the time to see each employee as an individual. Her people felt truly valued, and she protected them from all drama and distractions so they could do what they do best. It was one of the most technically high-performing teams I’ve worked with. 


Her biggest weakness? When faced with a new problem or strategic decision to be made, she’d spend a small amount of time getting input and then quickly form an opinion. Once that happened, she refused to accept alternative ideas. And she really didn’t like when people tried to push that boundary. She never became angry or intimidating; instead she would just shut down and tune out. 


Those unknowing or persistent souls who continued to press got shut out for good. People learned that they could only take it to her edge, but no further. 


As effective as she was at running her team when things were routine, this habit made it extremely difficult when the team was faced with a new opportunity or unexpected issue. Her solutions were less innovative and creative as a result.


What to Do Instead


Assume positive intent

Your team is here because they believe in your company, and that they have the potential to make an impact, and they want to be part of something meaningful. Assume that their thoughts and opinions come from a place of positive intent and shared purpose, no matter how they express it. 


Ask hard questions

Encourage your team to tell you the truth by intentionally seeking their opinion on hard questions. What’s not working here (and why)? What am I not thinking of? What’s the #1 thing that would make you want to leave this company? are some of my favorites.



#3 You Gravitate Toward People Who Agree With You


Many leaders fall into the subconscious trap of surrounding themselves with people who agree with them. It’s like confirmation bias, and it’s rooted in our desire to validate what we already believe to be true. It doesn’t matter what’s at stake, because the subconscious is driving the process. 


What does it look like? When you’re trying to make a decision or get feedback from the team, you seek out the opinions of people who think like you do. You pay more attention to their comments, draw out their responses, ask more follow up questions. You make more direct eye contact with them, maybe even lean your body in their direction. They get more “air time” and your implicit approval.


In contrast, you hesitate to seek input from those who think differently. You rarely turn to them first when asking for an opinion. You may look away from them when they talk, or even make eye contact with someone else in the room to feel an alliance of sorts.  


Since much of what’s being communicated is subtle and unspoken, it’s easy for the subtext to go unnoticed unless folks are specifically watching for it. Even if your team picks up on it, it’s challenging for them to confidently describe the behavior, unless it’s a longstanding or broadly recognized pattern. As such, it also tends to happen far more frequently than other “watchout” behaviors, so the impact can be even more damaging over the long term.


What to Do Instead


Intentionally hire and support people who are different than you

Deliberately pick team members who think about things differently than you do. Not only does it cultivate the open culture you’re striving for, but it’s been proven that adding racial, ethnic, and gender diversity leads to better outcomes. 


Be 100% invested in their success

There’s nothing worse for your company, your culture (or the person) than to hire someone who thinks differently than you do, then be triggered by said qualities, and let them flounder (or fire them) because they turned out not to be a “fit”, or because they didn’t produce the results you expected because they were off on an island. As powerful as it can be for creating a culture of open communication, the negative impact of this person failing will leave a lasting mark on your culture. If you’re willing to take the leap and hire those who think differently than you, be prepared to double-down on the strategies above to make it a success.


The longer you practice these behaviors, the more natural they’ll become. And by doing so, you’ll have taken a huge step forward in creating the company culture you aspire to have. Where people are encouraged to share their opinions, where the best decisions get made, and where you also get the best possible results. 

How To Run An All-Hands Call: A Case Study

In the early days, it’s easy for you and your small team to know exactly what’s most important. Energy is high and collaboration seems to just happen, without putting too much effort into it. Together, you collectively crush it every day to bring your concept to life.

But as your small team doubles, and then doubles again, the ease and flow of working together becomes a major pain point. This is a common challenge, especially for fast-growing companies.

Unfortunately, once you grow beyond about 10 people, the days of effortless alignment are over. It’s impossible to replicate with a team of 10 or 20 or 50 what you once had with a team of five.

But, you can create the next best thing; the version of what it should be at your new scale. Where everyone is working with high energy and is pushing in the same direction.

Achieving a collective focus in your growing team takes a few routines, done really well. One of my favorite practices is the all-hands call.

Quick Primer

All-hands calls are the ultimate alignment tool. Much like they sound, they’re meetings that bring together every teammate in the company to hear the same message and have a common experience. It’s where the CEO and other leaders convey direction and focus, going deep on topics and issues that matter most to the company. Because of this, they’re also key to building company culture.

All-hands calls are usually held quarterly to maintain the flow of communication and engagement, emphasizing what needs to be achieved in that quarter. Once in place, they’re also the practice you’ll lean on to keep the team together during periods of rapid change, or a crisis within the company or beyond.

Lately, I’ve been working with founders on their all-hands agendas in the context of the COVID pandemic. People are wrestling with a myriad of practical challenges and emotions that there’s no playbook for, that they inevitably bring to work. Protracted social distancing, working while homeschooling kids, anxiety about the illness and financial insecurity can all weigh heavily. Then there’s the impact to companies, which can range from minimal to crushing.

This is all to say that when planning an all-hands call, one size does not fit all for your agenda. Context is key.

Case Study: COVID-19 All Hands Call

I’ve been working with Groove for the past couple of years*. After a major product launch last year, they started 2020 strong, with an ambitious strategy to expand their influence in the customer support space. While growth has slowed since the COVID pandemic, cash flow is solid so they don’t expect any crushing blows. Their strategy and expansion into a broader platform remains the same, but the roadmap will change based on new projections and some recent insights from their net promoter scores.

With this in mind, here’s how we planned their latest call, along with tips for how to plan your own:

All Hands Plan

#1 Plan Ahead

Time: 1 hour work effort plus 1:1 time with employees, two weeks before

Two weeks before the call, set aside time to reflect on where you’re at as a company, how you’re feeling about progress on your main priorities, and what the team needs right now. This will ensure your agenda is relevant and you’re making the most of the time.

If an employee survey is part of your normal routine, try to sequence it so that you get results before the meeting. This way, you know what’s on people’s minds ahead of time and can proactively address important and timely topics.

What we did: 

Since Alex Turnbull and his cofounder weren’t sure of the team’s frame of mind in the midst of the pandemic, they decided to move up their quarterly 1:1 meetings with each team member to get an accurate pulse. They learned that the team is generally energized and the impacts of COVID don’t seem to be their key focus. This enabled them to tailor their key messages based on where the team is at; going deep on the business versus broader or more personal impacts.

#2 Decide on Your Key Messages

Time: 1 hour work effort, one week before

Now that you’ve taken time to personally reflect and done your homework to find out what the team needs, decide on the two to three key messages you want to share with the team. When the call ends, what do you want to make sure people know? How do you want them to feel? What do you want them to do the same or differently as a result of what they’ve learned?

People process info in different ways and different speeds, and need lots of repetition. Use a small number of slides to reinforce key points and important details.

What we did:

Alex sketched out two main topics that were most important:

1) Where the company is at right now given the pandemic, and

2) What’s changing re: priorities and why.

He also wanted to create an experience for the team to feel connected to each other and their impact on the company. He wanted them to know that the company is going to feel some effects, but they’re staying the course on the strategy, with some modifications. He wanted the team to leave the meeting feeling excited, focused and confident in their ability to get it done. And he wanted everyone to think about how they might need to readjust their own work priorities based on changes to the roadmap.

#3 Set the Agenda

Time: 30 minute work effort, one week before

Next, set an agenda that achieves your key messages, with enough time that you don’t have to rush and attendees  stay engaged throughout. Make the experience dynamic by having multiple speakers, by varying formats, and by including opportunities for employees to participate.

Here’s what the agenda looked like:

Agenda: 60 minutes

  • Team activity (20 min):  Each team member shares what core value they’re most vibing on right now in their work. We chose this to encourage engagement, reinforce what makes individuals and the team great, and reinforce their strong culture.
  • Where we’re at right now (15 min): Review company roadmap and metrics, the bigger economic picture, how customers are responding, and cash flow overview.
  • Update on goals (20 min): What’s changing and why
  • Close (5 min)

#4 Prepare Your Talking Points and Other Logistics

Time: 15 minute work effort, 1 day before

Confirm all final details. Finalize your slides; decide if you’re going to facilitate team participation through chat, live discussion, or a combo of both; and confirm flow of handoffs.

Do a mental run-through and jot down specific points you want to make. Practice talking out specific messages that you want to go smoothly. This also ensures that you make the most of your team’s time and keep folks engaged.

#5 Have a Great Call!

Time: 60- 90 minutes

Take a few minutes before the call starts to mentally prepare for how you want to show up. Make sure everyone’s on video. Remember to record the call.

Decide on a position that’s comfortable and helps you maintain high energy throughout the call (e.g., standing at a table versus sitting at your desk).

#6 Debrief

Time: 5 minute work effort; more if you listen to the video recording

Get informal feedback from your leadership team and teammates who will give you an honest opinion. Verify that people understood your points and ask whether there were questions that weren’t covered in Q&A. Check how people reacted to the messages and how they’re feeling about what they learned.

Review the video recording to assess how effectively you conveyed your key messages. Was your tone and tempo engaging? Were your points crisp or did you meander? What went well and what would you change for your next call?

With just a few hours of strategic preparation, an all-hands call can be transformed from simply a company event to something much more. Use your next one to get your team pointing in the same direction, collectively working on the things that matter most, and sharing in your company culture.


* Thanks to the Groove team for agreeing to let me share the deets on their company and our work together.

7 Strategies for Leading Your Company Through Tough Times

Every founder faces tough moments–it’s inevitable. It could be that your strategy isn’t getting the results you were desperately counting on. Or, new users and your bottom line are lagging. Perhaps your latest release is riddled with defects and even your most loyal customers are leaving you.

Or it could be that a global pandemic interrupts life as we all know it. COVID-19 is new, but unforeseen business and leadership challenges are not.

Without a doubt, these are times that test us. But when every day feels like you’re going into battle; those are the times that count the most.

When so much is expected of you and so many are counting on you, it can be exhausting and overwhelming. I’ve coached hundreds of leaders through their toughest times and I know you can get through this, too. Here are my top seven tips:

#1 Get Your Head Right

You can’t be there for your team if you haven’t taken care of yourself first–both mentally and physically. Taking time to recharge will make you exponentially more productive and present for the rest of the day.

How do you know if you need to reassess your habits? Watch out for warning signs like your daily run getting replaced by a few glasses of wine, or a new Diet Coke habit that takes the edge off the sleep you’re not getting.

Suggestions: Meditation has been a game-changer for me. Headspace is my personal favorite. (Yes, I swear the subscription is worth it, and no, I’m not a sponsor; I just love it). That’s not all: do something at least three to four times a week that makes you sweat and that’s easy for you to fit into your schedule (a run, a Peloton ride, an on-demand workout, etc). Block time in your calendar to hold yourself accountable.

#2 Watch Your Pace

You may feel like taking time for yourself is a luxury you can’t afford, or that your company can’t spare you for that hour. When your company is going through an intense or tough period, the pace can be addictive.

The harder you work; you lose perspective on the big picture. The longer it goes on, the less possible it feels to take time for yourself or your family, or to find balance. You don’t realize it in the moment, but that relentless pace undoubtedly results in diminished performance, decision-making, and how you “show up”.

Suggestions: During the most extreme circumstances (monthly churn is in a death spiral; you’re scrambling for your next round of funding; your app keeps crashing), this pace will be unavoidable. In which case, do the best you can to eat well, get enough rest, and power through.

However, if this has become your business as usual, acknowledge it for what it is and take steps to force yourself to rebalance. This includes putting Slack on Do Not Disturb and shutting your laptop at night. Spend time with people you love. Go out to dinner. Go for a walk. You will wake up with a fresh perspective and a better mindset.

#3 Manage Your Style Under Stress

Hopefully, you already know about your personal strengths and limitations. You may have gained this insight through a Founder Feedback process (a structured process where you get feedback from the people you work closest with), or from trusted mentors and teammates.

It’s human nature that, when we’re stressed out, our weaknesses are more prominent. For example, if you tend to have a quick temper on a normal day, you’re even more likely to have one when you’re stressed. The same goes if you tend to avoid conflict, or if you secretly think you’re the smartest person in the room, or if you’re overly critical of others, or whatever it is you’re personally working on. The things you’re normally challenged by will get amplified if you don’t actively and aggressively manage them.

Suggestions: To avoid your style going negative, take note of triggers and remove yourself from the situation. When you feel like your level of stress is causing you to lose perspective (which happens to the best of us), ask people you trust to be on the lookout for the warning signs. Lastly, remember that managing your mindset and pace will help you stave off negative styles.

#4 Communicate More, Not Less

There are so many reasons why leaders tend to communicate less during tough times. Maybe it doesn’t feel like there’s enough time in the day. Or you don’t feel like you have the emotional capacity to rally the team because your stress is at its peak. Maybe you just can’t bring yourself to pull the team together because you feel like you have nothing encouraging to say.

It will be one of the harder things you’ll have to do, but put aside those doubts and excuses, dig deep, and do it anyway–frequently. One of your most important jobs is to be present for your people. They need you to support, guide and encourage them, especially during uncertain times. The longer you wait, the more the anxiety will creep into your team and affect their morale, performance, and productivity.

If you don’t fill the communication vacuum, other people will create the message for you. Their message will almost always paint the darkest version of any situation.

Suggestions: Throughout the month, use a combo of communication mechanisms to connect with your teammates:

  • Send an informal note to the team.
  • Share a daily or weekly video with your personal thoughts and words of encouragement.
  • Share personal perspectives and get firsthand feedback at 1:1’s.
  • Communicate key messages and create alignment on all-hands calls.
  • Build connection, trust, and culture at theme-based all-team calls.

#5 Be Human

When you talk to your team, be yourself. Don’t be afraid to share how you’ve personally been affected by the tough times you’re going through. It’s OK to let people see the doubts and stress you’re facing.

For example, after 9/11, our leader who wasn’t known for her soft side unexpectedly broke down in tears in front of the whole team. In addition to managing the impacts of the company in crisis, she was concerned about her daughter who lived in Manhattan. Her team saw a side of her that she had previously kept from them.

Rather than seeing it as a sign of weakness, our understanding and appreciation for her as a person and a leader expanded significantly. This is what people mean when they say to be authentic and human: Be open with your feelings so your team can share the experience with you. There’s nothing that builds connection more than a leader who lets the team know that they’re going through it too.

Suggestions: Talk about the things that matter to you and how you’re being affected. Share examples and tell stories.

Though, to be clear: Don’t misconstrue authenticity to mean spontaneity. Have an idea of what you want to say ahead of time to prevent over-sharing or coming across as insensitive to your people’s challenges (which could be greater than yours). Turn your video on and let people see your body language in addition to hearing your words.

#6 Don’t Sugarcoat It

Don’t sugarcoat the challenges you’re up against. Humans have a keen sense for bullshit. The quickest way to destroy trust and credibility with your team is to massage the truth or avoid it altogether.

In most cases, your team will be able to handle reality, and it’ll help them know how to direct their energy toward the things that are most critical to your company in that moment. They’re the ones who will pull the company through the challenge you’re facing. Being transparent and telling the truth builds the deepest kind of loyalty.

Suggestions: Your team will be hanging onto every word, so be deliberate about how and what you say. As above, spontaneity is not your friend at these times. Decide on the key messages you want to share with the team. Practice ahead of time if you’re nervous. If you’re worried about what your facial expression and body language might convey, video yourself as you practice.

#7 Give Your Team Hope

When things may seem uncertain, and in some cases even dire, there’s always a reason to be optimistic. Remind your team about what’s uniquely awesome about your company. It’s those things that will give them hope and inspire you and them to dig even deeper. Let them know that you’ll get through it together.

Suggestions: Grab a quiet moment and think back to the highest points with your team and your company. What made you great then? What still applies now? Your Core Values are a great place for inspiration.

This tough time will pass, but it won’t be the last one you face. Reflect on what you can take from the experience to make you and your company stronger.  Every day we have the ability to learn, evolve, get better. You will get through this and emerge a stronger person and leader for it.