What Undisciplined Meetings Are Costing You

Let’s imagine a scene.

Team members filter into a conference room for five minutes. This is followed by another few minutes of chit chat. In the midst of casual conversation, someone brings up an urgent (to them) issue that consumes another ten minutes for whoever is paying attention. The group eventually focuses on the agenda, though a few people seem mentally checked out or are busy multitasking. Twenty minutes before the meeting is supposed to end, the team gets around to discussing the most pressing issues. Even though the meeting goes over by 15 minutes, no decision is made and no alignment is reached.

Sound familiar? The real question is: How much are undisciplined meetings costing your company?

It may not seem like it on the surface, but if your meetings look like this, you have an expensive problem on your hands. Simply put, your team has a finite capacity to get things done each week. Every minute spent in an undisciplined meeting is mindshare and productivity lost.

Let’s say there were six people in the meeting I described above. Do some quick math: multiply the amount of people in the meeting times the amount of time the meeting lasts. That one hour meeting that ran over took up 7.5 hours of your company’s time. Now ask yourself, how satisfied are you with the value you created with those 7.5 hours?

If your answer is “not enough”, then here are a six easy rules to create better meeting habits:

Rule #1 Every meeting has a purpose and a desired outcome.

Simply put, what are you there to do? Do you need to solve an issue? Brainstorm ideas? Make a decision? Ensure everyone is aligned around a plan? Consider adding the meeting purpose to the invite so your team can come prepared and you don’t waste valuable time.

Rule #2 Every person in the meeting understands their role in it.

Are they present to provide input? To understand the details of a decision that affects their work? Or to coordinate on a complex project? Encourage your team to ask for clarification when they’re unclear.

Rule #3 If a person doesn’t have a role, they don’t go to the meeting.

If someone’s purpose for being in the meeting is unclear, encourage them to decline the invite or leave the meeting; no apology or explanation needed. In fact, celebrate when people take that action. It’s the quickest way to create a healthy meeting culture.

Rule #4 Start and end on time.

One of the quickest ways teams lose focus (and energy) is when the scheduled meeting time is not respected. When you commit to work within your meeting time, it creates positive pressure to focus on the most important topics and it keeps the discussion more organized and concise. This makes forward momentum in the way of decisions and next steps more likely.

Rule #5 Always discuss what’s next.

A meeting is only as valuable as what comes out of it. Use the last five minutes of your time to recap any decisions that were made and what needs to happen next.

Rule #6 Give yourself a grade.

Have the team share accountability for improving meetings by having everyone rate the meeting at the end. How valuable was the discussion? How well did you move forward on key issues? Was it an effective use of the team’s time? By giving your meetings a grade, you can also track your progress over time.

There’s a final benefit of good meeting habits that may even outweigh the others. Meetings reflect your company’s culture in action. They are the proof of what your culture is; not what you wish it would be.

Discover These 6 Things From Founder Feedback

Photo by Jenny Ueberberg on Unsplash

When was the last time you wondered how your team really feels about you as their leader? Does the thought of finding out evoke curiosity or give you a pit in your stomach?

If you dread getting feedback, you’re not alone. In fact, even the most seasoned leaders can feel self-doubt about it at first. (Rest assured- it gets easier the more you do it!).

And though it may be tempting to avoid, Founder Feedback is actually one of the most important elements of your leadership practice.

Why? Quite simply, it’s the best way to know what you do that brings your team high energy, and what may take it away.

In extreme cases, leaders resort to getting feedback when either they as the founder- or their team- have reached a breaking point. They have no other choice but to find out what’s at the root of the friction.

But if you make Founder Feedback a regular leadership routine, it’ll never be a lagging indicator of what’s not working.

In fact, think of the data as a leading indicator — of what makes your team feel inspired and motivated, as well as potentially distracted or drained.

Here are 6 things you’ll discover through a high quality Founder Feedback process:

1. You’ll see yourself through your team’s eyes.

As human beings, we normally only see ourselves and our actions through our personal set of filters. We create our unique lens from our life experiences, which in turn shapes our beliefs, assumptions and interpretations.

In contrast, your team’s feedback enables you to view yourself through their lens. You can see how others experience you and can compare your team’s perceptions against your own. Why is this change of perspective so important? Because your success as a leader is directly correlated to whether they believe you motivate, inspire and align them.

2. You’ll discover the strengths you undervalue.

Many of us — especially those who battle self-doubt — can overemphasize our shortcomings and undervalue our strengths. Quite simply, we don’t believe our talents and gifts are as exceptional as others do. By seeing yourself through your team’s eyes, you can appreciate the exact ways in which you positively impact your team. This will allow you to draw on those natural strengths more intentionally, especially at crucial moments.

One founder who recently went through this process discovered that his honesty and sense of humor were key to getting the team through an intense funding round and product pivot. While he knew he possessed these qualities, he didn’t realize how profoundly it helped the team get re-energized and inspired during a dark period.

3. You’ll learn about your blindspots.

Like the strengths that we undervalue, we’re often unaware of our behaviors that get in the way of our true goals. During these moments, our style under stress can get activated and cause us to act less consciously and intentionally. And what we communicate- verbally and nonverbally- has an outsized impact on the person receiving it. Left unaddressed, blindspots can become one of the biggest blocks to long term success.

A founder with a passion for debating ideas learned that some on her team felt she needed to win these discussions at any cost. They felt put down by her tone and that their ideas weren’t valued. With this insight, the founder was able to make some small adjustments to her approach to create a more productive outcome.

4. You’ll understand your full impact on the team.

By getting input from multiple people, Founder Feedback creates a composite view of how you influence the team. You’ll understand how your presence affects their collective ability to create, share ideas, collaborate, problem solve, and express different points of view. Then you can intentionally choose approaches that best motivate your team.

A founder’s team sensed him shift into intense command mode whenever a timeline slipped. During these moments, he tended to make abrupt decisions that caused huge changes to people’s existing priorities. His intensity also elevated the team’s stress level, making it harder to focus on getting things done at an especially important time. The feedback motivated him to get help to manage his stress more productively.

5. You’ll gauge the team’s alignment.

How is your team interpreting your key messages? Are they excited by your new strategy or concerned about the pivot? This is your chance to understand how your team is responding to your story about where the company is going and what you want them to know, feel and do.

One founder learned that his team hadn’t entirely bought into his decision to launch a new product channel. Based on their feedback, he realized he had to spend more time providing context about the opportunity in order for the team to feel as confident about it as he did.

6. You’ll measure the level of trust in your culture.

The quality of the feedback you receive indicates how safe your team feels to share what they really think. This depth of honesty is a crucial marker of company culture; if your team filters their opinions, then you can’t fix their issues. Which means the issues will likely fester and eventually erode morale, retention and productivity.

One founder learned that her new Product lead was feeling his skills were underappreciated. He was even starting to question whether he should have taken the job. Because her Product lead had been completely candid, the founder was able to immediately address his concerns and get them aligned.

The process requires one final thing: an open mindset. Remember that you’re a work in progress. The feedback reflects how you’re showing up at this moment. With new insights, you can consciously choose your approach with your team in the future.


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.