“When I’m coaching founders, I never want us to get too far from the question: ‘What does the business need from you right now?’”
It’s not hard to see why Alisa Cohn favors this question. It may seem to center strategic thinking, but it’s a deeper exercise in disguise, one that requires founders to recognize how the company has changed — and confront the gaps where they may be falling short.
Self-awareness is a particularly tricky skill for founders, CEOs, and execs to sharpen. The seemingly simple task of understanding what you’re doing well and uncovering the ways in which you need to grow becomes increasingly tough for several reasons. In the hazy days of changing business models, experimentation (and hopefully) hypergrowth, it's hard to know if something is working because of the leader’s behavior or in spite of it. At the same time, the faucet of upward feedback also slows to a trickle — as hierarchy takes hold, fewer and fewer feel comfortable challenging the founder’s big ideas, or pointing out their missteps. Furthermore, the parameters of your own role are constantly changing as the team grows and challenges stack up. “You almost have to re-onboard yourself as CEO,” says Cohn.
And that’s just half the battle. Even if you do manage to surface high-quality feedback and identify your opportunities for growth, implementing change in your day-to-day routine is another matter entirely. The calendar fills up, the hectic pace of startup life takes over, and months go by before you realize you haven’t moved the personal growth needle.
Cohn is the perfect person to provide direction here. With nearly 20 years of experience as an executive coach, she’s worked with companies ranging from Etsy, Venmo, and InVision to The Wirecutter, Google and IBM, even counting folks like Tim Ferriss among her client list. To scale the impact of her coaching experience and share lessons learned with more leaders, Cohn penned a new book, “From Start-Up to Grown-Up.” It details how founders can scale their leadership as the company grows, and it’s full of tips on how to manage yourself, collaborate better with others, and yes, stay focused on what the business needs from you.
“You can be a successful CEO with all different behaviors and styles. You can be loud, you can be soft, you can be charismatic. But what’s consistent is the need to change as the company grows,” says Cohn. “If you're a quiet CEO, you might need to bring much stronger and more extroverted communication skills when you’re recruiting, fundraising, or talking to the press. If you’re more externally focused, you're going to have to focus more internally on culture and organizational issues as the team grows. As the founder, you need to be self-aware enough to realize when the company requires something different from you. And if you don't, the culture just kind of grows around you — and it's not always a good fit for the kind of company you're trying to build.”
Take this real-world example: “I was working with a first-time CEO, and her remote team had grown much more quickly than she had anticipated, reaching 60 people in what felt like overnight. And in our first session she said, ‘I don't feel like I'm showing up well for the team.’ She didn’t always feel like a leader because she was so busy putting out fires herself, and still executing as an IC. There was a lot of confusion on the team and things breaking down because they were moving so quickly. We identified that the team needed more communication, so we set up a cadence of All Hands and executive team meetings,” says Cohn. “And I had the CEO block off 10 minutes before those key meetings, to step away from her to-dos and remind herself that her team was looking to her for leadership, not for the task list she was working on. We created a few phrases that worked for her, like ‘What do they need to hear right now?’ or ‘It’s not about you, it’s about them.’ You can find phrases that resonate for you and help enlarge your own perspective before you approach important leadership moments.”
As a founder, you likely felt a connection between your personal style and the kind of product and service you wanted to build. And so it makes sense that your startup will initially shape itself around you. But over time, as the company grows, you as the CEO need to bring something different to the table — your style can’t stay static.
In this exclusive interview, Cohn offers up her advice and strategies for doing just that. From getting better at self-reflection, to encouraging others to give you more feedback — and more crucially, figuring out what to do with it — she shares a practical guide to how founders and early startup employees can scale into the C-Suite leaders they need to become. It’s a unique window into what we can learn from her executive coaching practice — from the anonymized real-life anecdotes, to the tactics she leans on when working with founders, to the tools and question sets that they can effectively leverage on their own.
STARTING WITH SELF-AWARENESS — HOW TO MAKE REFLECTION A REFLEX:
Before diving into soliciting feedback from your peers and reports, Cohn recommends starting with yourself. “If you know who you are, you’ll see where you need to get better — and where you might need to hire someone else who is better than you,” she says.
“Founders need to learn to reflect, get in the habit of reflecting, and turn to reflection — rather than reaction — when bad things happen,” she says. “Even when there’s a crisis and the leader needs to act quickly, she still needs to take the time to stop, look, and listen: ‘What’s going on here? What is getting to me? How did I cause this situation, either by what I did or what I didn’t do? What should I do now?’”
The act of reflection needs to become reflex. Radical self-examination requires a sincere desire to see and own your own “stuff” so that you can grow.
Given that a large portion of a startup’s culture stems from the founder and the network effects of hiring, this self-assessment is all the more critical in the early days. “When starting a company, the founder is in some ways creating a culture that is a reflection of themselves. And unless they've been very deliberate about deciding what culture they want to have, they tend to just hire a bunch of friends or people they know — and very often unconsciously hire themselves,” says Cohn.
“There's a CEO I work with who, without knowing it, hired a whole executive team, all of whom had done individual sports — not team sports. And so the culture was a reflection of that. They were more a collection of individuals operating their functions, rather than a team working together,” she says. “And that means that when the company needs leaders to go after a goal together, they may be more likely to deal with things individually and less likely to coordinate together. It also may mean that leaders don’t naturally step in for each other. That might be okay when you have 10 people, but that gets very ineffective at 30 people. And once you reach north of one hundred and growing, forget it.”
If you haven’t done some self-reflection, you hire yourself over and over again without realizing it. Your company becomes a mirror of yourself — with all the good and all the bad.
Of course, this requires flagging what you’re already bringing to the table — your natural leadership style, how you show up every day, the “stuff” you need to work on, and the rituals to keep you grounded. Below, Cohn offers advice on how to navigate this self-reflection.
Questions to ask yourself:
“When I start working with a CEO, I will often ask, ‘What's the end game here?’ And more often than not, they don’t say that it’s to cash out and get rich. They say it’s to build a legacy, or to create wealth for all the employees, or to further the mission of the company and make everyone's life better in a certain way,” says Cohn. “So then I help them think about the three, five or the 10 year vision of who they want to be. That takes it from less of a ‘Here are all the problems you have here today,’ and more into, ‘Well, you said you wanted this, and that this is the kind of person you want to be — what do you need to do to make that happen?’”
How do you need to show up differently today to achieve that five-year vision of who you need to be in order to run the kind of company you want to build?
If you’re not partnering with a coach, Cohn suggests reflecting on these questions on your own:
What three words would you want people to use to describe you?
Your company is a mirror. What do you want to see there?
Where do you need to dial up or down the elements of your leadership style?
What are your superpowers and what is your Achilles’ heel?
In addition to applying an aspirational lens, Cohn also helps her clients focus on key aspects of their natural leadership style with these questions:
How do you express yourself to people? “Do you ask them questions, listen to the responses, and supportively explore solutions together? Or do you tell them what to do and hold them accountable for the result?”
How do you deal with conflict? “Do you lean into conflict to try to eliminate it, or do you avoid it and hope that people work it out for themselves?”
What’s your natural swing on giving feedback and having difficult conversations? Do you tend to wait to address issues or weigh in bluntly whenever you see a problem?
How much do you want to control the process? “Do you watch over every step in the process or wait for the end result? Do you tend to assume you should handle most things or do you instinctively ask yourself who else could do a certain task? How much personal participation do you prefer and how much can you give up? Do you make decisions by yourself and let people know or do you gather opinions and get consensus from the team?”
How do you respond to stress? “Do you check out or shut down? Do you snap back? Do you work harder?”
How do you make decisions? “Do you put them off waiting for more information or are you quick, maybe even impulsive? Do you go with your gut or insist on data? How much do you bring in others on your team to weigh in?”
Lean on this ritual to build in more reflection time:
“Some of the most effective CEOs I work with have a practice of continually asking: ‘What am I missing?’ or ‘What's the counterfactual to what I think is going to happen here?’ And I think that's a very powerful tool. I encourage all the leaders I work with to incorporate daily reflection,” says Cohn.
“On my podcast and for my book, I interviewed Suzy Batiz, the founder and former CEO of Poo-Pourri, and Sadie Lincoln, the founder/CEO of barre3. And they’re both incredible examples of fearless conviction, following intuition and doing it their own way. They both built really big businesses, bootstrapped with no investment. That doesn't mean you should make every decision based on intuition or not take facts or data into account, but it highlights that knowing when to tap into your inner voice and use intuition to guide your decisions can be very powerful,” she says.
Here’s how Cohn gets founders to be more aware of this tool: “Journaling helps you tune into your intuition as well as get a handle on how your emotional state may be playing into your decision-making. Setting aside time to journal, even just five to 10 minutes a day, helps you tune into clues about what’s going on in you and around you.”
In the busyness of our day-to-day lives, we tend to push aside our instincts. If we don’t proactively make time for the kind of thinking that builds self-awareness and intuition, we may make decisions based on forces that we’re not really conscious of.
If you’re looking for a place to get started, Cohn recommends this self-examination exercise:
What am I thinking and feeling right now?
What energized me so far today?
What discouraged me so far today?
What thoughts or feelings did I have during these moments?
How did these things affect my actions?
Given all that, what should I do right now?
FINDING BETTER FEEDBACK — AND FIGURING OUT WHAT TO DO WITH IT:
“But even if you’ve been scrupulously honest about your inner life and thoughtful about your natural style and current state, you may come across to people quite differently than you think you do,” says Cohn. That’s why her go-to recommendation is always to run a 360-feedback process. “Although this can be uncomfortable, it’s always enlightening. The goal of 360-feedback is not to make you feel bad, it’s to help you align your behavior with your intention.”
You are the expert on your intentions. Everyone around you is the expert on your impact. Leading effectively is about marrying intention with impact.
How to encourage and collect the feedback you need:
Don't have a coach or an advisor who can facilitate the process for you? Cohn offers a lightweight way to start: “The first place to begin is to invest in setting up the right relationships with the folks around you so they can offer up suggestions on a regular basis,” she says. “People don't want to volunteer feedback, but asking ‘What do I need to get better at?’ over and over and over again signals that you’re serious about getting better. You could ask your executive team, or folks one or two levels down. It’s also good to ask people who have been with the company a long time — if they were there when it was just 10 people, they’ll have a different kind of relationship with you.”
But asking is just part of the equation. “You need to reward that behavior. It could be publicly saying, ‘I got this feedback from so and so, and I really appreciate the suggestion, and I'm going to start doing that.’ If the CEO will share that in a public forum and recognize that feedback is appreciated, it helps people feel safer giving feedback and creates an environment where people are expected to be learning.”
If you’re curious about how the 360-feedback process works with an executive coach quarterbacking it, Cohn offers a window in her approach: “I speak with everyone around the executive I’m running the feedback process for. It’s important to get the perspective of the consumers of your leadership — they’re the ones who are able to weigh in on how your leadership is landing,” she says.
“I try to establish rapport very quickly because I want to make sure they're able to tell me the uncomfortable things. So I really spend time trying to make people feel safe and letting them know that the feedback is confidential. I give the comments and the feedback back to the CEO, but I'm not going to say who said what. And I remind them that if they have any inklings or observations that they're not quite sure if they should bring up, it's a good time to share them all in service of the CEO being a better leader, and ultimately the company being more successful.”
Here’s what Cohn tends to ask to pull that information out:
What do her strongest allies say about her?
What are her strongest strengths?
What do her harshest critics say about her?
What are her development opportunities? Her weaknesses, blind spots, and obstacles?
When she is trying to influence you, how does she do it?
How do you describe her leadership style?
What environments bring out the worst in her?
Do you think she's more external facing or more internal facing? Do you think it's the right balance?
What specific behavioral suggestions do you have to help her be a better leader?
“That last question is always the same,” she says. “That’s where I really dig in. Because often I hear things like ‘Oh, she's not collaborative enough,’ or ‘He’s not a great strategic thinker.’ And I always ask, ‘What do you mean by that?’ Because that can mean a lot of different things to a lot of different people. So I want to get at their behavioral suggestions — what their specific idea of what collaboration or strategic thinking looks like,” says Cohn. “Should she let everybody know once she's made a decision, or ask for all of the execs’ opinions beforehand? Does he need to be more of a long-term thinker? Or is he not proactive enough, which is sometimes what strategic thinking means to people.”
There’s nothing more frustrating than being told “She’s not collaborative enough,” or “He needs to be more strategic,” with no sense of how to change that.
What you might hear:
If you’re curious about the content of what you might expect to get back, Cohn shares a few common patterns in the feedback that most founders she works with tend to hear:
Communication: “People regularly feel like they need more communication from the CEO. You think you’ve told people what they need to hear. But they feel like they need more. They want to know the vision — even if it hasn’t changed since the last time you talked about it. They want to know what you’re thinking, what you’re hearing from customers, and what your expectations are. And employees want to know that you see them and the impact of their work,” says Cohn. “There’s an adage that you have to communicate the same thing over and over until you’re sick of your own voice before your team will really take in what you’re saying. It’s something that is hard to really internalize as a CEO until you specifically get the feedback that you need to communicate more.”
Conflict: “Maybe the founder never engages in conflict. She needs to be able to give constructive feedback, or she needs to hold people accountable and engage in difficult conversations. The other side of that might be a CEO who can be overly direct and actually make people feel bad because he’s regularly very critical.”
Not giving enough praise: “As a founder you may be more internally motivated than most and are particularly attuned to the problems. But when your people only hear criticism or problems coming from you, they get a lopsided view — they feel like they're failing even when they're doing well. That uncertainty costs you because it embeds itself into their heads as self-doubt and that makes them a little less safe, a little less energetic, and, as a result, a little less likely to offer a revolutionary idea.”
Decision-making: “This commonly comes up. One side of it is that a CEO often feels like everyone has to weigh in before she makes decisions. Inexperienced CEOs often feel like they should be running a democracy. One of the unsung secrets of leadership is that the majority of people want more direction than founders realize,” says Cohn. “On the other end, some CEOs make decisions on their own without consulting the other relevant people and that leaves them both blindsided and kind of demoralized, like ‘Well, what am I doing here?’”
You have to find the right balance of when and how much to consult others — and when to make the call yourself. When you’re out of balance you’ll hear about it in the feedback.
How to evaluate the feedback you receive:
“I feed whatever comes up back to the CEO anonymously and we go through it. It's very helpful for folks to have a roadmap of what their direct reports and team members want to see from them as consumers of their leadership. But many founders have some sort of initial reaction, which we have to deal with first,” says Cohn. “It’s the ‘That’s not fair,’ or ‘It's not true’ responses, and different kinds of defensiveness or guardedness. But at some point they quickly move to the topic at hand. And so we look at it and process it together.”
Here’s how Cohn guides executives along: “The most important thing I can do is I can ask them, ‘Just try it on. What do you think it looks like from their point of view? Can you see this? Can you imagine the impact they're experiencing?’” she says. “Because often the leader will respond with something like, ‘Oh, they don't understand that I’m behaving that way because I'm just trying to make sure that everyone does the same thing,’ or ‘They don't understand all the pressures I’m balancing.’ While that may be true, their perception in this case is reality and we have to deal with the reality of their perception.”
Considering the feedback doesn’t mean taking on every recommendation as an action item, however. “It's important to note that the CEO doesn't have to — and often shouldn’t — take all the suggestions that come out of this process,” says Cohn. “For example, a CEO I once worked with got the feedback that he should stop insisting that people create more repeatable processes because it was impinging on the creativity of the team. Since he valued creativity this was hard for him to hear. As we talked this through, we came back to the question of what the business needed. The answer was clear: more structure and consistency. He rejected the suggestions, but he addressed them with his team by explaining why process was so important.”
In other words, not all feedback is created equal. Some of it stems from the feedback giver’s own perspective. “Very often feedback is a reflection of the person's concerns, preferences or their own shortcomings. This is the problem with just asking a couple of folks for feedback. I typically sit down with eight to 12 people, and so clear themes emerge from talking to a good sample size of people,” says Cohn.
To get a better sense of whether it’s signal or noise, she offers up these questions to ask yourself as you evaluate the feedback:
Is the feedback an outlier or minority point of view? Then be on the lookout for the concern, but focus on the areas that were more concentrated.
Is the feedback targeted to concerns about and resistance to culture change you're trying to make? That might be a sign that your culture change is working, but people are having trouble with it. Rather than stop the changes you're trying to make, add more communication and support from you and your leaders.
Does the feedback relate to concerns from your early employees that they don't feel as connected to you or that you've gotten more formal or less fun? That's one of the inevitable outcomes of growth of your company. You need to continue your maturation process, and they may need some help accepting this.
Does the feedback relate to you managing more closely an employee who is not performing well in a critical role? You probably don't want to take the feedback to "zoom out" with this employee just yet, but you might need to have more clear and direct conversations with this person about your concerns and expectations.
CEOs are under the mistaken impression that they have to take all of the feedback, all of the time.
TURNING FEEDBACK INTO ACTION ITEMS — THE ART OF ACTUALLY MAKING A CHANGE:
Next comes the truly hard part: turning this introspection and feedback into a plan of action. Despite a genuine commitment to making a change, in most cases if you were to follow up on a round of feedback in six months or so, you wouldn’t notice much of a difference — and that’s because these habits and behaviors are much more deeply rooted than you might expect.
“We all have identities that we bring into the workplace, and they’re often very difficult to change. One CEO I worked with was extremely critical and never gave positive feedback. And it was pretty deeply rooted. He had grown up in an environment with a father who did not give him a lot of positive feedback and was very critical. We bring these things with us into the workplace and they affect our relationships,” says Cohn.
“Another founder I worked with was having trouble hiring. It turned out that his identity had not yet caught up with being the CEO of a fast-growing company. His identity was still ‘I wonder if I should leave my job and start this startup.’ He was still in that space emotionally. And he was concerned about telling other human beings that they should leave their safe job and come and work for this little, rickety ship that he had.”
Some of these hurdles are more rooted in the career ladder. “Another example would be a founder who grew up in the product or engineering space and still sees herself that way. And so she’s hesitant to take on the mantle of authority or decisiveness, and she wants to create a collaborative environment where we're all weighing in equally, just like we used to when we were working together in the trenches. She has the opportunity to be more decisive and directive, even though it makes her very uncomfortable,” says Cohn. “The way to resolve these challenges that stem from your identity is both outside in and inside out.”
We can think our way into a new way of acting, and we can also act our way into a new way of thinking. To me, that’s one of the real superpowers of a great CEO.
Here’s her three-step playbook for doing just that: “Step one is to decide you want to make a change. And then step two is to set a clear goal. What does that change going to look like? So going back to the CEO who struggled to give praise, it’s going to be that at the end of a number of months, people are going to experience you as someone who gives positive feedback,” says Cohn. “Another example could be you need to work on delegating more regularly.”
To follow through on that, start by writing it down. “You can actually say, ‘Okay, my goal for myself is to make sure everybody on the executive team gets at least two or three words of praise per week,’ or ‘My goal for myself is to delegate more often.’”
Cohn offers up a few tactics for ensuring that you follow through:
Start a spreadsheet. “Whether your goal is to give more positive feedback or to start to delegate more, you can maintain a spreadsheet to keep tabs and make sure you’re actually doing that,” says Cohn. “For example, you can track for yourself the number of things you delegate per week. Your first week or two will be your baseline, and as you work on delegating more, the number of items you delegate should go up.”
Maintain your streak. “This is similar to tracking on a spreadsheet, but some people like this method better. You can use a daily habit tracker app to remind yourself of the change you want to make — it's very motivating to have an unbroken streak of successes.”
Trigger a habit. “Another way to approach the change that this requires is by thinking about learning triggers: Every time I see X, I will do Y,” says Cohn. “So in the case of delegation, you might say, ‘Every time I start approaching a task by myself, I will ask myself: Should someone else be doing this?’ Over time, this habit will start to cue you to delegate more regularly and more naturally.”
But the third step in the process is the one that’s most often overlooked. “You need to change both the reality of your behavior and the perception,” she says. “I worked with a large company for several years. And when I first showed up, the CEO told me a story to illustrate that one of his executives was not holding his team accountable. Five years later, that CEO was telling me the same story about that same executive, even though the executive had actually made significant changes in having tough conversations with his team. Often people don’t really see the changes you’ve made unless you find ways to point them out.
Checking in with people to see if they've noticed your change is an extremely powerful — and often overlooked — part of the feedback process.
“The best way to make sure that people are observing the changes you're trying to make is to ask them if they've noticed the change, or to ask for specific suggestions on how you can make this change more rapidly, or more consistently. And then do that again and again. That really cues and signals to people that you're trying to make these changes and you want them to notice,” says Cohn.
“So returning to the praise example, you maintain a spreadsheet, keep giving out more positive feedback, and then make sure to follow up. In a few weeks you can say, ‘Hey, I heard from my coach that I wasn't giving enough positive feedback. And it's really important to me that we have an environment where people can work well together and grow, so I wanted to let you know that's what I'm working on. Have you noticed a change?’ Now the first time you flag that for them, they may not have noticed a change — but now they're on the lookout for that kind of new behavior,” she says.
“What’s important about going back to the team is that these follow-up meetings open up a space for the conversation around change. The discussions create the safety to talk openly about what’s going on. What used to be taboo topics become things that the CEO and her people can talk about. When you tell people what’s going on with you and what you need to change, they can open up and tell you what’s happening inside of them too. Vulnerability yields vulnerability. You are working on yourself — and that gives everyone permission to work on themselves too.”
Cover image by Getty Images / Luisella Sem / EyeEm.