Alisa Cohn

Alisa Cohn is an executive coach who has worked with C-suite executives at startups like Venmo, Etsy, Wirecutter, and DraftKings, and Fortune 500 companies like Microsoft, Google, Pfizer, Dell, and IBM. Inc. Magazine named Alisa one of the top 100 leadership speakers, and she was named one of the Top 50 coaches in the world by Thinkers50 and the #1 startup coach for the past four years by Global Gurus. She is also the author of From Start-Up to Grown-Up, which won the 2022 Independent Press Award and the American Book Fest 2023 Best Book Award for Entrepreneurship, and is the creator and host of a podcast of the same name.

6 skills 15 insights

Communication Skills

Ending meetings with standardized questions ensures alignment and prevents the need for 're-meetings.'

"My three questions to end the meeting are, what did we decide here? Who needs to do what by when? And who else needs to know?"
50:01

In larger meetings, use a sampling technique to verify alignment on decisions before adjourning.

"If you're in a meeting with a large executive team... you probably want to get a few people just to... I would just even say as a facilitator, two or three people, 'Okay, two or three people, what do..."
54:52

Hiring & Teams Skills

A healthy culture is built on results and clarity, not just employee happiness or perks.

"They're trying now to be the leader who everyone loves, but what really needs to happen very often is, we need to drive towards results... High engagement workforce is great. I think what that comes f..."
39:09

Explicitly aligning on core values prevents friction caused by different underlying assumptions about work and behavior.

"What are your values? And I think it's really essential to do some sort of values clarification exercise. You can find a ton of them online. You can find a list of values and just pull out your core v..."
57:36

Leadership Skills

When delivering disappointing news like a denied promotion, it is crucial to provide a sense of hope and a path for future growth.

"Hope for the future is so important. I know this is going to be challenging for you to hear, not going to promote you, but I want you to know this. It's really important to me that you're able to succ..."
00:10

Reframing difficult conversations as opportunities for growth and clarity helps overcome the fear of upsetting others.

"No one wants to make anybody upset, but through that upset on the other side of that, can often be a whole new possibility and a whole new revelation, and actually a lot of joy and freedom. I think th..."
07:51

Effective performance feedback should be based on observable facts and shared goals rather than personal judgment.

"Matilda, I want to chat with you about the way you're interacting with your peers. So what I'm hearing from them is that you're missing deadlines on a regular basis and not letting them know you're mi..."
12:55

When giving feedback on specific skills like writing, provide clear examples of excellence for the employee to model.

"Matilda, part of your job is to be able to create these documents and I appreciate that you do them on time. What I've observed is that they can often be not as structured as I'd like them to be and t..."
17:43

If a conversation becomes defensive or emotional, pausing to reset the intention can prevent it from escalating into a fight.

"Let's pause for a second because I'm feeling the energy has changed and I can see that you're getting a little bit heated by what I'm saying and I want you to know that I have no intention of upsettin..."
24:25

When denying a promotion, be direct, explain the specific criteria used for the decision, and maintain the employee's dignity.

"Matilda, I know this is going to be challenging for you to hear. I know you were hoping to get that promotion, but I want to let you know that we are going to actually be looking for an external candi..."
25:24

Before firing someone, you must have a 'crystal clear' conversation where the consequences of failing to improve are explicitly stated.

"I need you to know that this is very important. I need you to fix this within the next 30 days. Otherwise, I'm sorry to say, we're going to have to find a way to part ways because I can't keep this go..."
32:23

The actual firing conversation should be a brief confirmation of previous discussions rather than a new debate.

"Matilda, we talked about this multiple times. The last time we had this conversation, I told you I needed you to make these changes. You haven't made these changes and we're going to part ways. So I h..."
35:05

Establishing a 'tie-breaking' protocol in advance prevents stalemates and resentment during disagreements.

"How do we decide when we disagree? And that is a very good thing to explore because there's actually a lot of different ways to decide when you disagree... let's assume that the person who cares the m..."
01:05:57

Sharing a 'Personal Operating Manual' reduces friction in collaboration by making implicit preferences explicit.

"Personal Operating Manual. And it helps prompt you to talk about working style together... What communication style do you like the best? How do you like to work? Do you like large uninterrupted block..."
01:15:21

Product Management Skills

Founders and leaders must explicitly align on what 'success' looks like to avoid fundamental strategic drift.

"Vision of the company. So when this company is successful, what does that look like?... What that might look like is a big venture outcome that we all read about. And if you are both assuming that you..."
01:02:01