From Start-up to Grown-up: How to Avoid Common Mistakes Founders Make with Alisa Cohn: An EOFire Classic from 2021

11 Jan 2025 · 23 min

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Podcast Notes: Entrepreneurs on Fire

Episode Title

From Start-up to Grown-up: How to Avoid Common Mistakes Founders Make with Alisa Cohn (An EOFire Classic from 2021)

Host

  • John Lee Dumas (JLD)

Guest

  • Alisa Cohn: Executive coach, author of *From Start-up to Grown-up*, and has coached executives at companies like Venmo, Etsy, and DraftKings.

Episode Overview

This episode explores the transition from startup phase to a more mature organization, highlighting common mistakes founders make and providing actionable insights on leadership, hiring, and effective communication.

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Key Concepts and Takeaways

Core Values and Reflections

  1. Setting Directions vs. Goals:
  2. Key Insight: Alisa argues against traditional goal-setting; instead, she recommends setting directions to guide actions and decisions.
  3. Implementation: Emphasize consistent actions over rigid goals.
  1. Building a Thriving Organization:
  2. Primary Focus: The heart of success lies not just in the product or technology, but in creating a sustainable organization with a structured environment and effective management of team psychology.
  3. Critical Elements: Structure, people management, and addressing employees' needs and challenges.

Mistakes Founders Commonly Make

  • Neglecting Team Dynamics: Founders often overlook the need for management structures, leading to chaos within teams.
  • Misguided Micromanagement: While micromanaging is generally discouraged, early-stage teams may require closer supervision to effectively complete tasks.
  • Hiring Without Evidence:
  • Relying on personal bias (liking a candidate) instead of evaluating specific competencies and evidence of their capabilities can lead to poor hiring decisions.

Effective Hiring Strategies

  1. Granular Job Specification:
  2. Clearly define job roles and expectations from the outset.
  3. Use targeted questions during interviews to gather specific evidence of past performance and skills.
  1. Onboarding Game Plan:
  2. Establish a 30-60-90 day plan to help new hires integrate and succeed quickly.
  3. Include quick wins that help build credibility and foster team integration.
  1. Firing Decisions:
  2. Recognize the signs of a poor fit early and have clear objectives for performance.
  3. Acknowledge that employees often sense when they are not a good fit, making the conversation around parting ways less confrontational.

Communication and Meeting Effectiveness

  • MAGA: Make Agendas Great Again:
  • Emphasizes the importance of structured meeting agendas to achieve goals effectively.
  • Suggested elements include:
  • Clear objectives
  • Specific activities to reach those objectives
  • Follow-up questions to ensure accountability

Delicate Conversations

  • Alisa provides scripts for handling sensitive discussions, emphasizing compassion and clarity when addressing employee performance and career development.

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Additional Resources

  • Alisa Cohn's Website: [AlyssaCohn.com/fire](https://www.alyssacohn.com/fire)
  • Offers scripts and templates for onboarding, difficult conversations, and creating an operating manual.

Sponsors Mentioned

  • HubSpot: Marketing tools and resources.
  • ThriveTime Show: Business growth workshops.
  • Airbnb: Co-hosting services for property management.

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Conclusion Alisa Cohn’s insights provide a valuable framework for founders transitioning into leadership roles, emphasizing the significance of managing people and processes effectively. This episode serves as a comprehensive guide to avoiding common pitfalls and fostering a productive organizational culture.

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Call to Action

  • Explore more about Alisa Cohn’s work and resources tailored for founders at [AlyssaCohn.com/fire](https://www.alyssacohn.com/fire).

Remember, the average of the five people you spend the most time with shapes your future. Engage with insightful leaders like Alisa Cohn and John Lee Dumas to keep your entrepreneurial journey thriving!

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Transcript

Automatic transcript. May contain errors.

0:01Boom! Shake the room, Fire Nation. JLD here and welcome to Entrepreneurs on Fire. Brought to you by the HubSpot.

0:30at Venmo, Etsy, DraftKings, along with enterprises such as Dell, Hitachi, and Pfizer. She writes for HBR and Inc. and has been featured in Bloomberg, the BBC, and New York Times. In today's Fire Nation, we'll talk about how you do not need to set goals. Instead, set directions. And the secret to great hiring is setting up a specific game plan about what you want to accomplish in 30 days, 60 days, and 90 days. And Fire Nation, so much more. And a big thank you for sponsoring today's episode goes to Alisa and our sponsors. Success Story, hosted by Scott D. Clary, is brought to you by the HubSpot Podcast Network, the audio destination for business professionals.

1:06Success Story features Q &A sessions with successful business leaders, keynote presentations, and conversations on sales, marketing, business, startups, and entrepreneurship. A recent episode discussing the billion-dollar health secret with the founder and CEO of Whoop is a must-listen. Listen to Success Story wherever you get your podcasts. Is this your year to grow a successful business? Attend the world's highest rated business growth workshop taught personally by Clay Clark and now featuring Rich Dad Poor Dad author Robert Kiyosaki and Eric Trump at thrivetimeshow.com slash EO Fire. Again, request life-changing tickets today at thrivetimeshow.com slash EO Fire.

1:51Alyssa, say what's up to Fire Nation and share something that you believe about becoming successful that most people disagree with. So what's up, Fire Nation? So great to be here with you. And one thing that I really think a lot about that people think you need to be successful that I disagree with is setting goals. I say, don't set goals. You can set direction and you should. You should definitely set up and lock in processes and systems and definitely support yourself in taking action and then take action day after day, week after week, month after month, year after year. It's that constant, consistent action and the process of doing it every day that's going to help you achieve your dreams, not the goals.

2:37And Fire Nation, this is coming from a pickleball pro, so you know to take notes and listen up. And we're talking about going from startup to growing up, how to avoid common mistakes founders make and what to do instead. So I really like specificity, Alyssa. So I just want to dive right into the single most important thing that founders get wrong when starting their business. Thanks for asking me that. Yes. So I think what founders do is they start their business and they think that their success and their journey is going to be about the product and about the technology and their solution. And it's not, it's actually about their ability to build a thriving, sustaining organization.

3:16It has to do with structure, with people and the way you manage your own psychology through the ups and downs, which is extremely challenging. Now, let's go through maybe an example. You don't have to use names. You don't have to use companies, whatever it is. But like, what's a real time action of a founder just getting this wrong? Well, I worked with a founder a few years ago at a company in Austin, and he called me because his team was about to be in mutiny because he had been so focused on drive, drive, drive, build, build, build the product that he hadn't stepped back and thought about what do these people need?

3:53And what they need is management. What they need is systems and what they need is structure. So it was kind of a free for all. It was kind of like, let's have no hierarchy. And then what that means is everybody's tripping over each other. Nobody's clear on what they're supposed to be doing and how they can define success and achieve success. And they're not being managed. So they don't get that sort of positive reinforcement. They don't get guidance and direction. So because of that, even though the product was amazing and what they were building was amazing, the company was really in trouble because of the neglect of those things.

4:25One thing that I feel like it's a really bad rap in our world specifically, Alyssa, is being a micromanager. Everybody's like, oh, don't be a micromanager. You can't have your hands in everything. You just need to let people go do their thing or to tell people how to do things once and then never look at them again. Like if you're a micromanager, your business will fail. Why is sometimes, not all the times, but why is sometimes being a micromanager the right answer? Yes, that is one of my own counterintuitive beliefs that people always tell founders, don't be a micromanager or founders themselves will say, I'm not a micromanager.

5:02And yet the truth is that when you hire a team, especially early stage, but even as you grow, they are not always the most capable people of doing the things that you want them to do. It doesn't mean they're bad. It doesn't mean they're not willing to try, but it may mean they don't have the skills and experience to do that thing. Like I had a founder one time who gave his, um, his, uh, actually assistant this, this job of, um, gathering information about the competitors of the company. He, he was just like, interested. And she went out and she did this whole incredible, like way too much overcomplicated job about it and brought it back to him.

5:41And it wasn't what he wanted. And he got mad. And I'm thinking, did you even, and what we talked about was, did you even really ask her or guide her in what you wanted? Did you set up the structure and the template so she could kind of fill it out and give her a chance to ask questions? And the truth is that that is just much closer supervision than he thought that she or anybody else would need to do a task. Everybody, every founder, every leader has to assess the will and skill of their employees to be able to delegate to them, to be able to manage them at the appropriate level of supervision.

6:13And sometimes that does mean what we call micromanagement. I love that phrase, assess the will and skill of your employee. That's really cool and definitely a thought to keep in mind, Fire Nation. Now, hiring is such a struggle And no, Fire Nation, this is not a sponsorship ad for ZipRecruiter. I'm just saying that hiring in general, it's such a struggle. So share with us how we can hire right the first time. And then on the flip side of things, how do we know when to fire somebody? Oh, yes. So true. So when I think about hiring, what I experience most of the founders I work with and most of the CEOs I work with, when they're not experts yet at hiring, they tend to go through a big interview process.

6:59And then at the end of the day, they kind of decide, I like Lisa, let's hire Lisa. Or I like Frank, let's hire Frank. And that's kind of how they make decisions about hiring. And that's not all there is to it. But after going through a process, they don't have often evidence about that, that this person can do the job. So the secret is number one, to get super clear and super granular about the jobs to be done, the thing that you want this person to do in like a very specific kind of way. And then go out and get evidence by asking that person questions. You know, if you want someone to be super proactive, talk about times that you, um, you ask them, ask this person about times that they did something without being asked that they did something that was above and beyond what they wanted to, that they had to do.

7:43If you're looking for someone who's great at influencing, talk about, ask this person about times they had to bring other people along who disagreed with them and how they were able to bring them to a different place without breaking any glass. You have to ask specific questions. And then when you talk to the references, ask specific questions to gather evidence that they can do those specific jobs to be done. So that's about hiring. Now life goes on and sadly people are not always up to the task and maybe they were up to the task or up to the job and you know, they, they outgrew it or it outgrew them.

8:17Um, or they just weren't the right hire. So what happens is I come into a situation very often. And we're talking about this one person. And as soon as a founder realizes that he should fire this person, the truth is, it's probably a year too late. That's like a truism in the startup world. And the way to think about that is setting clear, specific goals for this person and making sure they have the right objectives and then seeing if they can meet those objectives. And if they can't over time, and you've had conversations with them over time and really help them see that you're serious about them to achieve these objectives, then you can finally realize that it's just not a fit.

8:57The secret is also that when you come to somebody and say, you know, it's just not a fit, I think we need to part ways. They've often come to that conclusion themselves and they're kind of relieved you finally brought it up. Wow. I mean, Fire Nation, think about those words when you're setting yourself up for success at the beginning of a relationship so that you can make sure you're doing what's best for both parties, both sides the equation going forward. And Alyssa, Fire Nation loves secrets. Share one secret to just a fantastic great hire. The secret to great hiring has to do with setting up a specific game plan about what you're hoping they accomplish in 30 days, what you're hoping they accomplish in 60 days, what you're hoping they accomplish in 90 days.

9:43You have a clear onboarding plan that includes specific deliverables, including quick wins, which are superficial and super fast, things that people do to gain credibility with their new team. So they start like, oh, this person's great. This person's going to add a lot of value. And then also making sure you handle the socialization, the integration of onboarding so people can actually have help getting integrated into the team and feeling part of the fabric and the culture. There's a theme here at Fire Nation, and that theme is communication. You need to be communicating, setting the right expectations, boundaries, all of this stuff, that's going to set up both sides for that win-win scenario.

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13:33Alyssa, we're back. And as I kind of tease before the break, MAGA, make agendas great again. Expound upon this. I am obsessed with meetings. I love meetings. I love the potential of meetings. Everybody else hates meetings. And I don't plan them. Like they're not well-planned. They're kind of a waste of time. And I just think that's such a shame because it's, first of all, an expensive room. And also it is the potential of so much wisdom because everyone there is so smart and so interested and wanting to like really eager to make a difference. The key to all that is making a great agenda, specifically making agendas great again.

14:14And really it has to do with really planning, right? So you said communication and it's totally true. And it's also being intentional and planning. What do you want to do? So an agenda really sets out, what is the goal of this meeting? Like seriously, what are we trying to say at the end of this meeting that exists or that's different? That's not true at the beginning of the meeting. That's number one. Number two, how are we going to get there? What are the different activities and the tools and the sort of the facilitation processes we're gonna do to get to that goal? And third, to end the meeting with three powerful questions.

14:48Number one, what do we decide here? Number two, who will do what by when? And number three, who needs to know? roadmap, Fire Nation. Do you have one? Like, do you even have a roadmap for what's about to happen, what's about to take place? And what are your thoughts? You know, some people like to talk about standing meetings, like, you know, having a specific, you know, shortened amount of time. I mean, what do you feel like is the best for people to go about setting up and creating meetings and putting those on the agenda? Yeah. You know, I talk in my book from startup to growing up the different meetings you need to have.

15:20And the first is every day with yourself, a meeting with yourself every day to plan your day, to kind of reflect, to think about things. And that should be 30 minutes. A one-on-one with somebody should be about 30 minutes. But if you're having an executive team meeting, you might want that to be an hour or even two hours. But to your point about check-ins, check-ins are like such a powerful way to just get everybody on the same page in a 10 or 15 minute period. It's also energetic, it's dynamic. And when you're in person, the idea is you're actually standing up. If you're on video, you can also stand up.

15:51That's why they're called stand-ups. And nobody sits down and it's very dynamic and they add a lot of value by way of communication and syncing up without taking up too much time. Now from time to time, and let's just be honest, we all get into these delicate situations. So share some specific scripts that Fire Nation can use to handle these so-called delicate situations. Yes. In my book, From Startup to Grownup, I have an entire appendix about scripts to handle delicate situations, including, for example, when someone wants a promotion they're not ready for. So, for example, somebody comes to you and they say, you know, I want to go put myself in for this manager role or this director role, the vice president role, and you realize they're not even close.

16:37And so then you have to sit down and say to this person, hey, first of all, I think you're great and I probably don't tell you that enough. Also, it looks like we're off sync on your career development and I need to rectify that immediately. I want you to know that the person we're going to bring in to do this job that you're looking for has this kind of experience that you don't have. At the same time, I want you to know we really value you and I want to work with you to put together a career plan for yourself, a career progression plan for yourself, so that you can ultimately achieve your goals, whether it's getting promoted in this role or ultimately finding other roles in the company that are great for you.

17:14So that's kind of the way to handle a delicate situation and also to then have a follow-up plan and be as good as your word about really helping this person progress. Otherwise, they're not gonna understand why they didn't get promotion. They're gonna be frustrated and ultimately they're gonna leave you and it's such a waste because they were a good employee and you could have kept them if you addressed it directly and compassionately. These scripts, at least the one that you just recently talked about, they really show your employee, Fire Nation, that they are the priority, like that they matter, that their life matters.

17:44And, you know, as much as we like to think otherwise, everybody's favorite station is WWIFM. What's in it for me? Like, what's in it for me? Like, you know, I hate to say it, but like, that's the reality. So if you just think that your employee is just willing to fall on a sword and sacrifice themselves for your company at all costs, you got to think again. They need to know that you have their interests. and in some cases, their best interests out for them. And scripts like these are going to help you get there. Now, you did briefly go over this, but let's take the last couple of minutes we have here together to really dive in to your book, From Startup to Grownup.

18:23Break this down for us. What is the deal with this book? Why do we need to read it? Thank you for asking that. I think that every entrepreneur can usefully read it because it's really about the process of going from founder to CEO, the idea of somebody who's building a product or a service to somebody who's building a thriving business. So it's divided into three sections, managing yourself, managing the people around you, managing them, the employees, and then managing the company. And really everybody, all new leaders, all founders, and really even solopreneurs need to think about how they're building themselves along those three dimensions and learning and growing along those three dimensions.

19:04So, you know, I talked earlier about managing your own psychology. When you manage your own psychology, it's like there are lots of ups and downs to becoming a leader to the workplace and certainly to being an entrepreneur. And so you need to think about how you're going to reflect on yourself, reflect on your strengths and your weaknesses, and then also find specific tools and practices. Like I talk in the book about doing a highlight reel so that when you're feeling down and depressed and you feel like, oh, it's not working, you proactively remind yourself of all the successes you've had. That's a highlight reel and one of the examples of the exercises I use.

19:41When you're managing other people, to your point earlier, you need to think about it from their point of view. You're the manager, but you need to think about their point of view and how you're going to help them understand that they're making progress, that they are doing a good job, that you praise them, and also that they have a career progression. So when you manage other people, you've got to keep those things in mind. And then ultimately, nobody has a business unless they're able to measure the business. And so we all need to learn about stepping back and thinking about the structures and tools we're implementing in our own business.

20:10You don't have a business, Fire Nation, unless you know how to measure that business. So Alyssa, I know you've created something pretty cool for Fire Nation. Give us the call to action about where we can learn more about your book, this gift, and anything else you want to share. Well, thank you so much. Well, everyone can come to my website, AlyssaCohn.com. And I've put together for your listeners some scripts and templates. And that's AlyssaCohn.com slash fire. And specifically, we talked about these scripts. I've put together additional scripts for your listeners to help them onboard new employees, have a difficult conversation with anyone, and then also some templates about how to create your own operating manual so you get a handle on your own kind of quirks and your personality style and your communication style so you can share that with people around you and also help them fill out their own operating manual and share it with you.

21:01So all of that for your listeners because I want you to benefit. that my mission is to light 10 ,000 candles. My mission is to help people get better and solve problems before they become problems and really learn things before they have to make their own mistakes. So I hope all this material helps everybody do that. Fire Nation, you're the average. Of the five people you spend the most time with, you've been hanging out with AC and JLD today, so keep up the heat. And if you head over to eofire.com and type Alyssa, A-L-I-S-A, in the search bar. Her journalist page will pop up with everything that we've talked about.

21:38And of course, go over for that additional awesomeness. She created this stuff for you, Fire Nation. Take action. AlyssaCohn.com slash fire. That's A-L-I-S-A-C-O-H-N.com slash fire. Alyssa, thank you for sharing your truth, knowledge, value with Fire Nation today. For that, we salute you and we'll catch you on the flip side. Thank you so much for having me.

22:33Network, the audio destination for business professionals. Success Story features Q &A sessions with successful business leaders, keynote presentations, and conversations on sales, marketing, business, startups, and entrepreneurship. A recent episode discussing the billion-dollar health secret with the founder and CEO of Whoop is a must-listen. Listen to Success Story wherever you get your podcasts. Is this your year to grow a successful business? Attend the world's highest rated business growth workshop taught personally by Clay Clark and now featuring Rich Dad Poor Dad author Robert Kiyosaki and Eric Trump at Thrivetimeshow.com slash EOfire.

23:12Again, request life-changing tickets today at Thrivetimeshow.com slash EOfire.

From the publisher

From the archive: This episode was originally recorded and published in 2021. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant.

Alisa Cohn is an executive coach and the author of From Start-up to Grown-up. She has coached founders and executives at Venmo, Etsy, and DraftKings, along with enterprises such as Dell, Hitachi, and Pfizer. She writes for HBR and Inc and has been featured in Bloomberg, the BBC and New York Times.

Top 3 Value Bombs

1. You do not need to set goals; instead, set directions.

2. When starting a business, the most important thing is building a thriving, sustaining organization with a structure and with people who have their own psychology management through successes and challenges.

3. The secret to great hiring is setting up a specific game plan about what you want to accomplish in 30 days, 60 days, and 90 days.

5 Scripts for Delicate Conversations at Work (plus one bonus script to make your life better - Alisa's Website

Sponsors

HubSpot When you combine the power of Marketing Hub and Content Hub, you can have your best quarter, every quarter. Visit Hubspot.com/marketers to learn more

ThriveTime Show Attend the world’s highest rated business growth workshop taught personally by Clay Clark and NOW featuring Rich Dad Poor Dad Author Robert Kiyosaki and Eric Trump at ThrivetimeShow.com/eofire

Airbnb If you’ve got an extended trip coming up and need a little help hosting while you’re away, just hire a co-host to do the work for you. Find a co-host at Airbnb.com/host

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