Great Company Cultures Are Made, Not Bought.

A new founder was venting to me recently that she can’t afford an impressive office space for her growing team. As a result, she lamented, her company’s culture was clearly going to suffer. 


It’s easy to see why she’d think that.


After all, the internet is filled with stories that equate a strong culture with “things”: laser tag outings, wine tastings, flashy retreats– and yes, award-winning office spaces.  


Good news, I replied. Your culture has nothing to do with your office space.


What Really Matters

In contrast, I described what really matters– like Core Values that mean something, or the way the team behaves when a mistake is made. But I could see that she struggled to fully connect with my explanation. 


Searching for a fitting analogy, I told her about a trail hike I’d recently taken. 



It was a quiet, sunny August morning, and I was hiking the trails of Block Island. When I rounded a bend, I came upon this tree: majestic and wild, with the sun glowing from behind. 



I paused in my tracks, captivated by its mystical beauty. And then I imagined how strong its roots must be, to keep its tangle of branches anchored to the earth. 


Your company is like that tree, I explained. And your company’s culture are the roots


Like a tree’s, your company’s roots are mostly invisible to the naked eye, but contain the substance and energy that feeds your company. They need to be strong and run deep in order for your team to thrive as it grows. 


Grow Strong Roots

Your company’s roots become stronger when you:


  • Know- and act in alignment with- your company’s Core Values. This means hiring people who share your values, and making tough decisions that keep you in line with your values.
  • Reward behavior that strengthens trust, collaboration and psychological safety– and avoid acting in ways that weaken or destroy it. 
  • Listen to- and act upon- what your employees tell you they need. Are your benefits too basic? Do they feel it’s too hard to get things done? Probe for what really matters.
  • Commit to continually improving- as a founder and as a company. Rather than being a sign of weakness, treating yourself and your company as a work in progress encourages people to be more open and creative.


If you’re still unclear about how to cultivate your culture, let these two questions lead you: 


Is what you’re doing nourishing your company? 


Will it help keep your company anchored for the unexpected setback? 


Here’s what a great company culture sounds like

We’ve all heard the glossy stories of companies that are celebrated for their impressive company culture. But here’s a well-kept secret: some of the best cultures can be found in places that you may have never heard of. 


These lesser-known startups aren’t focusing on their culture for the viral success story. They simply know who they are and they build around what they value. 


Since every company has unique Core Values, there’s no one right way to foster identity. Which means that external validation is a pretty meaningless barometer for creating the environment that your people can thrive in. A far better indicator is what your employees say about working there.


In fact, you can find the answer in the very words your employees use.


I recently spoke with several engaged employees who described what it’s like to work at their company. This is what it sounds like when you’re part of a culture with a lot of constructive and creative energy:


“There’s space for everyone to have a voice.”

“Everyone is true to themselves and the work we’re doing.”

“We can rely on and understand each other.”

“I’m emotionally attached to this business.”

“I’ve been in the trenches with this company and this company has been in the trenches with me.”

“I can be who I am; I don’t need to be a character.”

“I have the freedom to try new things, be creative; I’m encouraged to ‘be more me.’”

“This company has taught me that you can actually not burn out at a job- not feel like your entire life is being sucked out of you.” 


When people are respected and accepted, they focus on their work, rather than worrying about how others will react. They’re curious and love learning new things. They share their opinions. They act intentionally and seek outcomes where all win.


As a result, the team has a broad and rich understanding about their priorities. And people tend to feel deeply connected to their work and their company.

To better understand your team’s engagement, listen to the words they use. Get the conversation started by meeting with each of your employees and asking them thoughtful, open-ended questions. You’ll quickly learn what does versus doesn’t matter to your people and your culture.


How to Include Your Team in Your Strategic Planning Process

There’s another way strategic planning is like sailing: You have to inspire your crew for the journey ahead. For tactical purposes, you tell your people where they’re going so they can take the right actions to get to the destination. But that’s not the only reason. When you help the team envision the end result, it keeps their energy and morale high, so they can tap into higher levels of effort and performance.


One of the first steps in getting a company aligned is sharing the company’s vision and strategy. Schedule an all-hands call to provide background and context on the company’s priorities. The most motivating leaders spend as much time talking about why the priorities have been chosen as what they are.


By fully explaining what the future looks like, your teammates will feel a deep responsibility for achieving it. What’s more, you’ll have a whole team of people independently channeling their creative thinking and unique expertise to achieve the end result as successfully as possible.


Imagine the difference between your employees simply focusing on the task that’s been assigned to them versus feeling a shared responsibility for creating the future. When your team understands the bigger picture, they can anticipate and troubleshoot things you never knew to think about. On top of that, their discretionary effort will shave off unproductivity and errors that affect your timeline and your bottom line.


Incidentally, all of this further amplifies the quality of your strategic planning, as well as how your team performs.  As CEO, you typically decide the vision with input from your leadership team and trusted advisors. But now your strategy can be informed by the insights and experience of your whole team. (Skip-level 1:1s are great for learning from your employees and testing ideas for your strategy).


In fast-growth companies, this virtuous cycle becomes essential to how the team operates. Leading to better results and a team that is emotionally connected to the company.





3 Key Questions for Annual Strategic Planning

Earlier, I shared my philosophy that strategic planning is a lot like sailing. When you’re under sail, conditions can change quickly. It’s natural to revise and refactor your plans along the way. 

In this case, instead of assessing the winds and weather, we use probing questions to dig into what’s enabling– and standing in the way of– your company achieving its most important priorities. Then we use those insights to confirm or adjust your plans. 

Successful founders use strategic planning–both annually and quarterly–to get to their vision as quickly and as profitably as possible. 

At each strategy session, you’ll look back on your progress, your challenges and other factors affecting what you’re trying to achieve. Then you’ll apply that knowledge to your upcoming plan. 

I always recommend quarterly strategy sessions, because a lot can change in three months for fast growth companies, and it enables us to pivot quickly. 

But it’s essential to take a top-level view at the end of the year as well; looking towards the full year ahead; a.k.a., the next big leg of the journey. 

In annual planning sessions, we ask three key questions: 


#1 Have we arrived at where we thought we’d be by this point?


Start by reviewing your company’s key metrics and goal plans. 

Did you achieve what you expected this year? If so, what people, processes, tools and other factors helped make that possible? If not, why not and what can you learn from it? 


#2 What adjustments do we need to make to stay on course? 


Take some time to reflect on your top priorities. 

Does your destination remain the same? Does it need to be adjusted now that you’re closer and have more information? What are your competitors doing and how might that change your direction? What changes or investments do you need to make to your people, processes and tools to stay on course?


#3 What are our new annual priorities? 


When you’ve arrived at the end of 2021, what does your destination look like? What have you achieved? What new features or products have you created? How much has your customer base grown? 

Once you’ve answered these questions, create a short, specific list of your top priorities for the year. This ensures that your team focuses their effort and energy on the most important outcomes.

Next, chunk your annual priorities into quarterly priorities to keep a clear line of sight. Then, cascade your annual priorities into a short list of team (or department-level) goals. Lastly, set individual goals for each team member that align to their team goals and the company’s top priorities. 

Next up: why and how to bring your people into your strategic planning process.

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.