What are you letting go of this year?

One question I’ve been asking my coaching clients lately: What are you letting go of this year?

This isn’t about adding to your to-do list. Instead, it’s about clearing the path. Think about:

• 🌟 Mindsets or assumptions that no longer serve you (or maybe never did).

• ⏳ Habits or ways of spending time that aren’t aligned with your goals.

• 🧩 Relationships or commitments that drain your energy.

We focus on what we want to achieve and commitments we want to add. But frequently the real magic of progress comes from removing things that are holding us back.

📈 Your Coaching Homework

This week, pick 2–3 things that might be holding you back. Then, choose one to let go of.

Here are two examples from my own life to spark your thinking:

1️⃣ Letting Go of Perfectionism

I’ve always had a high bar for quality, which has driven many of my successes. But when it comes to content creation, that same perfectionism can slow me down.

Here’s my hack: Instead of writing, I’ve shifted many of workflows to speaking. For some reason I feel less perfectionism while speaking, so now I do a podcast where I can prep and then let it fly, I use audio transcription to get ideas out while I’m walking my dog, and I even use voice shortcuts to respond to some emails. When I shoveled our cars out of the driveway on Monday, I did it while speaking into Fireflies.ai and thinking through my goals and plans for the week. Then when I got back to my computer, I had ChatGPT organize it and prep my week. For me, speaking frees me from over-editing and helps me get ideas out faster. This shift has made me happier and more productive.

2️⃣ Saying No to Group Zoom Calls

I realized that group Zoom calls often drain my energy. While I love in-person workshops, in-person meetings, and one-on-one Zooms, group Zoom calls rarely energize me and frequently drain me.

So, I’ve intentionally reduced them. I’ve stepped back from business lines that relied heavily on recurring group Zooms. It’s not a one-size-fits-all decision (not everybody can do that) and I’m not saying I don’t do these at all, but I’ve greatly reduced the volume and it’s been a game-changer for me.

🌟 Your Turn

Your examples might be totally different—maybe even the opposite of mine! The goal isn’t to copy but to reflect on what’s uniquely holding you back and give yourself permission to let it go.

Clearing space, whether mentally, physically, or emotionally, is what allows the great things to grow.

Happy pruning in 2025! Let’s improve clarity, focus, and momentum by reducing.

Until next time, enjoy the ride.

Building a peer group as a startup executive

As you become more senior, the job becomes more lonely. Engineers can go to happy hour, share stories, talk a little trash, and help each other shake off the day’s stress. When you are CTO, you are the only one in the company with that job and you don’t have a direct peer group. You have senior engineers, other execs, and maybe the CEO, but you can’t go to happy hour with 3 other CTO’s from the company and riff on your day because there aren’t others. So you have to reach outside the company to build that peer group.

Targeted peer groups can improve your happiness and performance in a variety of ways:

• Relieving stress - sharing notes and coping strategies with people who have empathy for your unique pressures

• Improving operational decisions - sharing experiences with vendor selections, talent and culture issues, and operational processes

• Improving relationships - discussing how to manage relationships with stakeholders

• Improving your network - getting to know other experts for future opportunities or recruiting

Therefore it is important to build targeted peer groups, especially for new executives. For CEO’s, I recommend YPO. Women may enjoy Chief. Some VC’s have guilds or groups for different functional leaders within their portfolio companies.

If you don’t have built in communities, you can go find them or create them. They can be casual or well organized like Round. Either way, it’s important.

Your homework for today:

1. Think about the unique challenges you face in your role

2. Consider where you want to be in 12 months

3. Review the frequency and quality of discussions you get with like-minded peers

4. If you are satisfied with 3, given 1 and 2, congrats - time for happy hour. If not, find a way to improve it. The communities are there. If you can’t find them, email me and I’ll help 🙂

It’s the end of product management as we know it.

My Cornell colleague Josh Hartmann and I recently spoke at a Cornell keynote about the rapid changes that have hit the tech world and how CEOs, CPOs, and CTOs are adapting. Let’s break down what tech leaders are doing and how you can think about evolving your product organization.

We have seen market crashes, most recently in 2001 and 2008. We have also seen several platform shifts: PCs, internet, cloud, and mobile. But we are on truly rare ground right now. A pandemic obliterated prior assumptions about office space, the market crashed, with SVB as a kicker, and we are on the precipice of a new platform shift with AI. All. At. Once.

So product management as we know it is done. It’s time to adjust our thinking, quickly.

One trend in the market is the revival of the General Manager role. This position has been around for a long time. It means running a P&L, including all costs that go into making and selling a product: product, design, engineering, marketing, sales, and operations. During the past ten years, many tech companies have used functional org designs with product, engineering, and design teams that report to their own executives without arbiters at the director or VP level who control resources cross-functionally. GMs were occasionally used in international teams or new ventures but rarely in core product development teams. In the functional model, P&L “ownership” is dispersed. During times of abundance, this org design works well because it optimizes for product decisions, tech tradeoffs, and distinct product, engineering, and design cultures. The big downside is that cross-functional decisions such as pricing changes, headcount changes, reorgs, or strategic shifts take longer because they require intense cross-functional negotiations. During times of abundance, those decisions can be slow and it is merely a nuisance. During times of scarcity, slow decisions will cause failure. We have been in abundance for 10+ years due to the incredible business models at big tech companies such as Meta and Google and the nearly endless venture capital fueling startups and growth companies.

Welcome to times of scarcity. It is now increasingly important to make hard tradeoff decisions rapidly. Creating GM roles or morphing other roles into GM roles is one tactic. I’m seeing a revival of the GM at tech companies and I like it.

It’s not the only way. AirBNB is doing something totally different. There has been a lot of talk about AirBNB implementing an Apple-style product marketing manager role that blends product and marketing. But listen to Brian Chesky carefully in his interviews; you see several key points many people are missing.

AirBNB’s efficiency is mind-blowing. They have less revenue and profit than companies like Google, but their Free Cash Flow per employee is in a league of its own. AirBNB has natural tailwinds because marketplace models at scale are highly profitable. But it’s still a remarkable example.

So what should you do in your org?

First, figure out who the decision-maker is in any given context or domain and lean into it. Great companies tend to be politically dominated by a specific function, usually driven by the founders' personalities. At Meta and Google, engineering runs the show. LinkedIn is product-driven. Apple and AirBNB are design-driven. Costco is operations-driven. The problem with these cultures is that dominant functions create the feeling of second-class citizens. Google PMs know they’re not the most important people in the room. But the advantage is giving somebody access to the accelerator and removing other people’s access to the brake pedal so you can move fast.

In today’s world, you better move fast. Figure out who should have the reins for specific decisions, and let them move.

Roles and responsibilities are frequently fuzzy, especially between product and other functions. An hour spent clarifying roles and responsibilities is a very high-leverage hour. Determine what artifacts must be created (roadmap, positioning statement, pricing page, etc.), what decisions must be made, and what activities must happen. Then make sure you have a function that clearly owns each.

Decisions need to be made by people close to the problem, with overall strategic context. If people on the ground make decisions but don’t fully understand the company’s strategy and investment areas, they won’t make the best decisions, and that’s not their fault. In contrast, ivory towers with execs making decisions on problems they don’t intimately understand will lead to failure and culture rot. So ensure your communications flow effectively; it’s the WD-40 for effective decisions. In today’s market, making difficult decisions with limited information quickly will give you the velocity you need to win.

If you have comments or questions or are taking a different approach on your team - shoot me a note!

Improve your team’s retention with structured career conversations

When I joined LinkedIn’s product team in 2012, I encountered a distinct approach to career conversations. It began with an upfront acknowledgement: “You are unlikely to work here for the rest of your career. Great, now that we addressed that we can be honest and discuss your true career goals.” This candid perspective, ingrained by Reid Hoffman, was based on a philosophy that employees join for a tour of duty to get the team from Point A to Point B. Completing this tour is important and leaving midway is a failure. But you should be open about your long-term aspirations and after each tour ends you have earned a discussion about your next career move, whether that be within LinkedIn or somewhere else.

While more common now, this was cutting edge in 2012. If a product manager aspires to become a venture-backed CEO, they might require more exposure to sales, even if not directly related to their current role. Ironically, the more marketable you make people externally the longer they stay because it means they’re growing.

Here are several tactics for engaging in these career conversations with your direct reports. It can be enlightening at times and uncover a deeper level of conversation around where your team members want to go, where they perceive they are growing and where they may feel stalled or blocked.

1. Proactively schedule a 30 to 60-minute conversation about their career

Avoid scheduling this during a crisis or before a significant deadline. Find a moment when you can step back from everyday tasks and focus solely on career-related topics. You may need to conduct a regular 1:1 meeting within the same week to discuss urgent matters separately, enabling both of you to be focused and present during the whole conversation. If possible, consider holding this conversation over coffee or a meal.

2. Share a document for them to fill out before you meet

Here is the format I use.

While simple, it can be challenging for many to complete. So, stress that this document is a dynamic work-in-progress and bringing a super rough draft for the first conversation is fine. Encourage them to start jotting down their aspirations and strategies for achieving them. Just as product success needs a roadmap, career success demands explicit goals and strategies.

3. Start with the long-term

Begin with a conversation about your direct report's long-term goals, both personal and professional. Choosing a 5-year horizon breaks some of the tension, especially if they are not accustomed to sharing their career ambitions with their manager. This timeframe seems distant enough to foster openness, yet near enough to require a specific plan. This dialogue can reveal a lot about their aspirations, how they feel about their career progression, and the types of challenges that will keep them engaged. It’s remarkable how often managers discover that a team member may depart in order to seek specific experiences or challenges when those can be readily facilitated internally with minimal adjustments. All because the manager asked and listened.

4. Discuss balancing individual aspirations and organizational objectives

Seek a balance between your team member’s passion and their job responsibilities. Ideally, most tasks align with both their goals and your needs. Acknowledge that 20% of the role may not cater to their interests, but it’s crucial for success in the job. Conversely, 20% of what they need for their career goals may not align with your objectives. That’s also OK and enables you to make room for them to engage in projects or side activities that stimulate the right types of learning and growth.

If the gap between job requirements and their personal goals is too large, it’s better to identify that, address it, and discuss it rather than leave it to fester. If the gap is closable in the short term, which it usually is, then you can collaborate on defining and bridging the gap.

5. Listen intently

These career conversations are invaluable for understanding how to best support your team. Make an effort to minimize distractions by switching off your phone and quieting your internal chatter. Truly immerse yourself in the conversation, listen to the ideas that are clearly articulated and guide them as they try to express ideas that are still incubating. If they haven’t yet defined precise career objectives, your assistance in discovering and refining those goals can be empowering.

6. Help them set measurable goals and actionable next steps

Let them steer the discussion, it’s essential that they feel ownership over the plan. But hold them accountable for creating a plan. Often, the initial attempt can be challenging and require iterations. That is natural, but ensure that they progress towards a plan with specific goals and action steps that you both agree on. Someone eager to hone their storytelling skills might find public speaking or improv classes useful, but never had an accountability partner to help them make it happen.

7. Schedule a follow up

Completing a significant project or "tour of duty" should prompt another round of conversation about future possibilities. Reflect on the milestones achieved and discuss what comes next. If there isn’t a specific milestone, then mark a date 3 or 6 months from now for a follow up. 

Engaging in career conversations with your direct reports paves the way for relationships founded on mutual understanding, support, and growth. The key is to be proactive, receptive, and sincere during these discussions. It will go a long way in cultivating a dynamic and motivated team where high performers are inspired to stay and do their best work.

Stand for something greater than yourself

My grandfather, Robert Grasty, was 16 years old when Pearl Harbor was bombed in 1941. Like the patriots of his era, he went straight to the Navy after his 18th birthday to voluntarily enroll. He was rejected due to a foot surgery. They said he couldn’t wear the boots. He was off the hook. But instead of going back to his life, he went to the Army. He was rejected again. So he kept trying until he successfully became a sailor for the US Merchant Marine. Not only did he choose to serve, he banged on doors until somebody said “Yes, you can risk your life for your country. Let’s get started.”

He recently passed away at 93 years of age. There are few World War II veterans left with us today. So let’s take some lessons from their generation as we pave the path for our own future.

Build for the long-term

My grandfather put himself through engineering school at Virginia Tech and then spent the meat of his career, 25+ years, at General Electric. He had a successful career and spent a good portion of it building jet engines. None of it was easy and nothing happened overnight. In today’s world, it’s easier than ever to find a new job or make a change. Personal autonomy is important and I have taken full advantage of that in my own career. I don’t think 25-year tours of duty should be the norm anymore. But we have to remember that it takes time to build things that matter. You don’t build a jet engine in a two-week sprint. You don’t win World War II in a single year. We need to mix the freedom, autonomy and creativity that is thriving in today’s workforce, with the idea that committing to things and building for the long-term matters. Because it does.

Invest in your family and community

Strong families and relationships don’t happen by accident. They happen because you invest in them and make them happen. At one point in his career, my grandfather was running a large manufacturing plant. His son, my uncle Peter, came to visit. Peter had been living on a commune, with the full hippie hair and dress code to match. Peter didn’t exactly fit in at my grandfather’s office, especially during times when there was serious tension between large corporations and the counter-culture movement. But my grandfather didn’t worry about other people’s opinions, even though his reputation and relationships were the key to his livelihood. He marched Peter in the front door, introduced him to the managers, and gave him a full tour. This sent a clear message, to Peter and to the team members at the plant, that family came first. My grandparents, like many from their generation, were constantly investing in their family and their community. Whether it was renting a lake house for family vacations, spending time with their church, coordinating dinner groups, or getting involved with local organizations, they brought people together.

Reach across the aisle

My grandmother, who inspired a post about building a successful career and a successful family, was a devoted democrat. She was actively involved with democratic activities and land conservation issues in New Hampshire. My grandfather was a staunch Republican. Yet they shared fundamental values and built a lifelong partnership, 63 years of marriage, and a loving family. I remember my dad asking my grandfather how many times their votes cancelled each other out in elections. My grandfather smiled and said “I don’t know. I never asked her who she voted for.” I assume he was half joking, but the message stuck with me. You can put politics aside in light of something greater than yourself. In a world that is increasingly politicized and partisan, let us remember that we can build relationships, organizations, and families across political barriers. It may not be the default. It may not be easy. But it is more important than ever.

Stand for something greater

It is hard to imagine what the world would be like without the sacrifices people made in World War II. What legacy will we leave for generations after us? I am not asking you to quit your job and join the peace corps. But think about your impact. Do things that make the world a little bit better. Build organizations that endure. Build real relationships with good people. Reach across an aisle or two. Stand for something greater than yourself.

In loving memory of Robert Alvin Grasty (1925-2018), US Merchant Marine (1943-1946).

10 Things Your Toddler Can Teach You About Running a Business

As a proud member of the crazy ones (entrepreneurs who run businesses and have families), I have seen my share of chaos. Yet raising a family comes with a sense of purpose different from anything else I have experienced. While I try to teach my son, he teaches me just as much in return. Here are ten things a toddler can teach you about running a business.

1. Communicate with short, clear messages

When a toddler learns to talk, you don't teach them long, complicated sentences. You start with the basics. The funny thing is, you can communicate most critical messages with very few words. You don't have a five page reason for why you buy Apple products (they're simple and beautiful), eat at McDonald's (it's cheap and convenient), or shop at Zappos (they have great customer service). So don't give a five page answer for why somebody should buy your product, work at your company, or invest in you. Keep your messages short and clear, that's what makes them powerful.

2. Create a fun environment

Kids quickly take on the vibe around them. If you're mad and stressed, they'll be mad and stressed. If you're happy and excited about life, they'll have high spirits and everything becomes easier. I can't claim that they'll want to sleep when you want to sleep (parents only wish), but you absolutely set the tone. The same thing goes at the office. Too many companies seem intent on creating workplaces where people are miserable. Make things fun, lighten up the mood, and take care of your team. Everybody will be happier AND more productive.

3. Repeat yourself ad nauseam

Repeating yourself as a parent gets old, but if you're ridiculously consistent you'll generate the right habits over time. BMW is "the ultimate driving machine" and I don't know that because they told me once, twice, or three times, I have seen it and heard it everywhere for years. Now I can't forget it (notice that the message is short and clear). It sounds silly, but repeating your messages constantly, everywhere, is what ingrains your branding in people's minds so that you become unmistakable.

4. Reward people frequently

Wall Street bonuses are probably the worst way to reward performance. They are giant, unpredictable lump sums paid at the end of the year. There is little transparency, lots of politics, and no loyalty to stay the day after the deposit clears. Would I reward my son after 3 weeks of good behavior? Goodness no. He should be rewarded right away. Adults really aren't any different. Here's the secret, the rewards don't have to big! Take your team to an awesome lunch, buy them iPads, congratulate them in front of their peers. Sometimes it's simply the act of rewarding people that matters, not the dollars that change hands.

5. Have a plan for everything

After having a kid, I became a lot less capable of flying by the seat of my pants. I used to wake up 20 minutes before leaving the house and as long as I showered, dressed and grabbed my wallet everything else would fall into place. With kids, you plan ahead for everything, coordinate schedules, and make contingency plans. That mindset holds well for running a business. Identify what you need to accomplish every day, week, and quarter. Discuss the opportunities and potential road blocks and plan for all of them. If you practice audibles with your team then you simply need to call the right play during the game and everybody knows what to do.

6. Understand that nothing will go as planned

Plans are wonderful and you should make them. But...life's never that simple. There's a balance between making plans and quickly adjusting when everything changes. Successful stock traders win not because they make better bets, but because they recognize their mistakes quicker and minimize losses. Top football teams win because they have a solid game plan and then make the right in-game adjustments. Treat your business as a game in progress. Your work is never done and you're always ready to adjust when necessary.

7. Practice what you preach

Don't feed somebody grilled chicken every day and talk about a nutritious diet while you eat french fries. It's simple and extremely easy to see. Lead or don't lead. But if you choose to lead, lead with your actions first.

8. Be authentic

Faking it doesn't work. Kids are very perceptive and remind you to stick with your true personality. This should carry over into your professional life as well. Forge a career that you are truly passionate about and work at a company where you fit the culture. Otherwise you're stuck faking it and that never leads to long-term success or happiness.

9. Build true loyalty and it will not be broken

Few bonds are as strong as a parent and a child. People will do anything for the family members they love. Build that relationship stronger and stronger over time and nothing will break it. The same is true for building teams. If your team is full of people who think of themselves first and have no loyalty, you're setting yourself up for failure. It's the tightly knit teams that stand up for each other and win the tough battles. Loyalty isn't built overnight and it doesn't come free - you have to earn it. So earn it.

10. Remember that shi$ happens

That's right, it happens. As a matter of fact, it happens all the time! Sometimes you have to clean up after a mess and move on without letting things bother you. Don't take yourself too seriously. That's one of the secrets to life.

Only Hire People Who Challenge You

Building a team is the most critical part of running a company (or any organization). There's a reason why the Yankees and the Patriots have so many rings: they have great teams from top to bottom. Do you think those organizations are easy to manage? Absolutely not. You should recruit team members who fit your culture, believe in your mission, and are fun to work with. But do not hire people because they make your life easy. Leadership is not about how many "followers" follow you, it's about how many leaders join you. Leaders are ambitious, opinionated, and won't let you off easy. They take a lot of energy to coordinate and aim in a single direction. They're also exactly who you need if you aspire to greatness. Building something valuable and sustainable isn't supposed to be easy. So don't take shortcuts, especially with your team.