As the saying goes, “All good things come to an end.” This is the last edition of the Lighthouse Leadership Weekly. It’s been a fun ride, and I’ve loved giving everyone a weekly dose of leadership thoughts to consider each week, dating all the way back to 2016 when I started emailing our weekly blog posts out to those who signed up.
However, the time has come for me to move on. But before I do, I wanted to give you one final special edition of this newsletter.
Why now? Opportunity + Passion = Drive
A formula I’ve been thinking a lot about in recent weeks is the combination of passion and opportunity.
When you love what you do, it shows in your work. I love talking about, analyzing, and writing about leadership. Helping lead teams to succeed in a positive, non-toxic way is one of the most fascinating and rewarding puzzles in the world to me.
I’ve also loved writing and sharing all our courses (which everyone will continue to receive throughout all of 2025, along with my support, responses, and service to those who purchased courses).
Yet, there is another important part of the equation: Opportunity.
You only get one shot at this life, and you have to think not just about seizing the opportunities around you and recognizing when there are good ones available, but also consider the opportunity cost of what you choose to do.
And in this case, with the AI revolution in full swing, I feel drawn to put my focus and efforts into experimenting there instead of writing this labor of love every week.
It’s been an honor and a pleasure to write this and help you learn new leadership skills, which is why I’m working hard to give you one final, awesome edition of this newsletter today.
Let’s dive in…
Table of contents:
- 🥘 Food for Thought on How Do You Want to be Remembered?
- 🗣️ Ask Lighthouse onCancelling All of Your 1 on 1s
- ❓ Poll of the Week on Onboarding and Performance Reviews
- 💼 What’s next, and what you can do to help…
Note: This is a preview of our weekly leadership newsletter, Lighthouse Leadership Weekly (LLW).To get this sent to your inbox every week, along with our latest long form essays on this blog, you can sign up here.
This final edition is brought to you by:
Chore: Your expert in HR, compliance, finance and equity
As a founder or executive, you want to focus on what you’re best at. Yet, when you have an early stage company, you often find yourself bogged down by having to be the one to take care of all kinds of back office compliance, record keeping, and financial tasks.
Who wants to spend their day doing that?!?
That’s why Chore was created. For much less than the cost of a full time employee, they take care of all your back office chores:
- HR & People Operations – Onboarding, payroll, benefits, and compliance, ensuring your team is supported and your company stays legally compliant no matter where your next hire comes from, or how fast you’re growing.
- Finance & Accounting – Bookkeeping, CFO-level insights, and tax support to keep your financials in check and investor-ready at all times. No more scrambling to get your numbers together for your accountant each tax season or for investor diligence.
- Compliance & Risk Management – Navigating state and federal regulations, managing your insurance plans, and staying ahead of audits while avoiding costly penalties from you missing filing deadlines.
- Equity & Cap Table Management – Handling your stock grants, mandatory 409A valuations, and key investor reporting with precision and accuracy without you worrying or having to deal with it.
Chore helps you get your time back and gives you peace of mind. They make sure your back office runs flawlessly, so you don’t have to.
If you have 5-75 employees on your team and want help with some (or all) of those back office areas, sign up to learn more about how you can hire chore to save you from all these tedious tasks, while bringing world-class expertise to doing them.
Schedule a free call to see how they can help you here.
🥘 Food for Thought on How Do You Want to be Remembered?
NVidia CEO Jensen Huang has been a frequent topic in this newsletter because he has a lot of interesting, and sometimes contrarian ideas.
I thought it was fitting then that in the final edition of this newsletter, that he tackled one of the biggest questions we all need to consider as part of living a full, meaningful life: How do you want to be remembered?
Jensen’s answer to how he wants to be remembered did not disappoint:
“Very simply, that [Nvidia] made an extraordinary impact. I think that we’re fortunate because of some core beliefs a long time ago and sticking with those core beliefs and building upon them, we found ourselves being one of the most important and consequential technology companies in the world, and potentially ever.
And so we take that responsibility very seriously. We work hard to make sure that the capabilities that we’ve created are available to large companies as well as individual researchers and developers, across every field of science no matter profitable or not, big or small, famous or otherwise.
And it’s because of this understanding of the consequential work that we’re doing and the potential impact it has on so many people that we want to make this capability as pervasive as possible.
…when we look back in a few years and I do hope that what the next generation realized is…they’re going to know us because of all the gaming technology we create, …the whole field of digital biology and life sciences has been transformed, our whole understanding of material sciences has completely been revolutionized. …Robots are helping us do dangerous and mundane things all over the place. That if we wanted to drive we can drive, but otherwise, you know take a nap or enjoy your car like it’s a home theater of yours,
…and you look back and you realize there’s this company almost at the epicenter of all of that and happens to be the company you grew up playing games with. I hope for that to be what the next generation learns.”
Wait, what does this mean?
At first glance, this is kind of an odd answer. You’d expect he would have spoken more directly about himself, his life, or specific milestones of his company. Nvidia certainly has plenty of specific wins that any company would envy and he could brag about.
Yet, instead Jensen focused on the mission and vision. It’s huge, it’s impactful, and it’s broad.
It’s the kind of thing that gives someone a reason to come to work even if their Nvidia stock makes them set for life. (A real problem the company has faced with much of its core team.)
This reminds me of the famous ad from Earnest Shackleton to recruit people to try to reach Antarctica:
"Men wanted for hazardous journey. Small wages, bitter cold, long months of complete darkness, constant danger, safe return doubtful. Honour and recognition in case of success."
Fortunately, Jensen’s vision doesn’t risk life or limb, but it does share an exciting vision where everywhere you look your work is making a difference and changing the future.
This is why we talk so much about the importance of purpose at work:
- You need a reason to get up every day beyond money to tap into your deepest wells of energy and inspiration.
- Your team will work harder and be more engaged if you give their work true meaning and they deeply understand their purpose and why their work matters.
- Recruiting is much easier when people are joining a mission they can believe in.
Now, you don’t have to transform transportation, gaming, biology, and AI to have a great mission and an attractive purpose. But just like Jensen paused for awhile before answering the question, you do need to take time to form a thoughtful answer.
A second lesson: Keep an eye out for new opportunities.
The second lesson is hidden at the end of Jensen’s quote:
“..and you look back and you realize there’s this company almost at the epicenter of all of that and happens to be the company you grew up playing games with. I hope for that to be what the next generation learns.”
For a long time, Nvidia was a graphics card company that helped people play the latest and greatest video games. That was a large business by itself, but they became the stock market darling and massively impactful company because they grew into much more than that in recent years.
And so the lesson I think Jensen hints at is that you should always be on the lookout for new opportunities. Those new innovations and use cases are what can transform your business from doing one thing to another even bigger and better thing.
It’s similar to Andy Grove’s journey he wrote about in “Only the Paranoid Survive” where Intel navigated rapid change in the 1980s to find new, even more profitable opportunities.
And it’s why Steve Jobs reminds us in his famous commencement speech, “you can only connect [the dots] looking backward” not looking forward. It’s hard to predict where you’ll end up, but opportunities knock and you have to take them when they call.
As leaders, this can mean many different things:
- Helping your team members seize new opportunities for growth and success as you see them build skills and thrive in various situations.
- Looking out for ways to help your company be more successful, solve new problems, and do things a better way through your own observations and listening to your team.
- Recognizing when it’s time for you or a team member to move on, because nothing lasts forever, and sometimes change is the right move.
As Jobs reminds us, you often already know what to do, if you just listen:
“Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma – which is living with the results of other people’s thinking. Don’t let the noise of others’ opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.”
What is your heart telling you?
📰 Ask Lighthouse: On extenuating circumstances for 1 on 1s
A friend emailed me a great situation to discuss the other day:
“Like you, I’ve always been a huge fan of 1 on 1s, but I was in a conversation recently where we decided the leader should cancel all of their 1 on 1s and skip level 1 on 1s.
It was crushing their calendar, and so based on their current priorities and high number of reports, it made sense to look for other ways to maintain his relationships and flow of information.“
This is a great example of the nuance of leadership.
In an ideal world, yes, you’d always have 1 on 1s, and if you’re a senior leader, you’d have skip level 1 on 1s as well. This helps you keep a pulse on everyone on your team and make sure you don’t miss anything important by waiting for it to organically reach you.
Yet, we don’t live in an ideal world, so let’s talk about some of the nuance of this kind of situation and the realistic solutions:
1) Can you reduce your team size?
One of the best indicators that you have too many direct reports is when you feel like 1 on 1s with them are taking too much of your time like in this situation.
The fact is, a single team with no hierarchy grows in communication complexity in a geometric fashion (each one more complex than the one before) as this image shows so clearly:
If you find yourself with 9, 10, 11+ reports, it’s time to think about promoting some folks to help take that load off of you. Then, you’ll suddenly find yourself with far fewer direct reports, and plenty of time for 1 on 1s with those that remain.
2) Take a flexible approach to frequency
While it’s a nice rule of thumb to meet weekly or bi-weekly with every direct report you have, it doesn’t always work in practice.
If you have a big team or a really tough schedule due to travel or other responsibilities, one of the best ways to free up your schedule is to re-evaluate the frequency of all of your 1 on 1s. That means considering who you really need to meet with the most and reducing the frequency for others.
Here are a few heuristics you can use to help with that:
- Meet more frequently with:
- New team members just getting settled and started.
- Anyone with Low Task Relevant Maturity on a key task or project, so you can regularly coach and support them.
- Struggling team members you need to turn around or let go.
- Meet less frequently with:
- Long time team members you have a great relationship with, and trust they’ll come to you with issues.
- Team members you can count on who have High Task Relevant Maturity for their main task(s) and project(s).
- Team members you see frequently in other ways so could spot issues even if their next 1 on 1 isn’t for awhile.
These tweaks won’t save a calendar that has dozens of meetings you need to prune, but it could save you a few hours a week.
Keep in mind, those in the “less frequent” category you still should meet with at least once a month. This is NOT permission to take your best people for granted.
Having been someone in that category, and a manager needing to shift some people there, good people often have a VERY long list waiting to talk to you about by the end of a month.
You are risking projects going sideways, management debt mounting, or even losing your best people if you stop having 1 on 1s with them entirely as Buffer learned the hard way.
3) Be picky with who you have skip level 1 on 1s with
Skip level 1 on 1s are a fantastic tool for keeping a pulse on lower levels in your organization as you rise in your career. There is so much you won’t hear, or will hear too late if you wait for only what comes to you.
Unfortunately, if you felt overwhelmed with 10 direct reports, then a rapidly expanding organization with multiple layers will really crush you and your schedule.
That’s why in addition to reducing your frequency of skip level 1 on 1s (like going from say once a quarter per person to once every six months), you may want to be pickier about who you meet with.
Yes, in an ideal world, you’d have skip level 1 on 1s with everyone, so you hear diverse perspectives and everyone has a voice. However, when you can’t, consider focusing the space on your calendar for skip levels on:
- People who have high visibility roles: You need to get to know your rising stars, both to give them support and see how you can help them take on the right projects, roles, and opportunities. Having skip levels with them is a high value investment for both sides.
- Team members who give great feedback: If you’ve ever had those 1 on 1s where the other person feels like a bump on a log, you know how hard it can be to get something out of some people. That’s why rewarding those that do bring critical insights can be a great way to manage your schedule and cut the ones that are a struggle to get value from.
- Those working in the most critical areas to you: Some projects are more important than others, so prioritize keeping a pulse on them by keeping your skip levels with key team members and those who have unique visibility.
- People on teams with managers you want to coach up: A great use of skip level 1 on 1s is getting feedback about the managers that report to you. If you know there’s a new or struggling manager on your team, shifting more of your skip levels to their team is a great way to quickly diagnose the most important areas to focus your coaching on for that manager.
Sometimes you really do need to hit the reset button and stop everything. If you can’t change your team structure, don’t see obvious folks you must have skip levels with, and you feel totally overwhelmed, clearing your calendar completely can be the right move.
Yet, for most of us, we live somewhere in the middle. In those cases, these tweaks can help bring sanity back to your schedule while still getting the insights, perspective, and coaching opportunities you need.
While that manager may initially feel relief by declaring calendar bankruptcy from these meetings, they will find themselves needing to add some of them back soon, or risk a lot of problems festering and building up on them in the coming weeks and months.
❓ Poll of the Week
The last 2 weeks, we had some great polls, so let’s take a look at what we found.
In poll #1, we asked you how much time you spend on performance reviews, and I was surprised to see how reasonable most of you were:
While I think we’d all love infinite time to review the work of each team member, it’s just not realistic with work schedules.
However, with the advancements of AI, I hope we quickly arrive at a future where your 1 on 1 notes and other data on your team member can be ingested and they will help you write a more fair, and comprehensive review that then removes things like recency bias.
—
Now, in Poll #2, we shifted gears to another really important question: onboarding.
As you can see, the primary challenge and focus of most leaders is getting that new hire productive and contributing. That makes sense; if you asked for more resources and to make an additional hire, the expectation is that you then put that investment to good use when you finally find the hire you were looking for.
Yet, to truly get someone up to speed, there’s more to consider, which is why I love some of the comments we got on the poll:
If you’re nervous about your onboarding process and want to know how some of the best leaders and companies do it, learn more about mastering the process here.
💼 What’s next, and what you can do…
If you’re curious what’s next for me, there will be a few things I’ll be focusing my efforts on:
- Making sure every manager has what they need to take their courses this year: Integrity is a really important value to me both personally and professionally, and I’m 110% committed to making sure everyone who purchased courses has a great experience and receives their lessons this year.
- How you can help: If you took a course and have a question or need anything, you can always reach out to me for help.
- Exploring opportunities in AI: There is an incredible amount of change, innovation, and opportunities in AI right now, and I am eager to dive head first into them to see what I can build with my mix of product, marketing, and hacky coding skills.
- How you can help: If you’re exploring AI too, have a tool I should look at, or are an engineer that likes helping new coders improve, hit reply because I’ll need all the help, advice, and insight I can get.
- Coaching Product Managers and Leaders: I also coach early stage SaaS product managers and leaders through some of their biggest challenges like mastering fundamental skills when you’re self-taught, fixing rising churn with your customers or team members, handling frustrated stakeholders, and fixing slipping product delivery dates, bugs, and disappointed customers.
- How you can help: If your team, or a friend’s team, has a struggling PM or product leader, you can reply to this email, directly intro your friend to me, or tell them to sign up for a free call at https://www.becustomerdriven.com/
Thanks to everyone who has been a part of this journey, whether as a customer of our software or courses, evangelist for our content and ways of leading, or simply reading this newsletter on a regular basis. I’m honored to have helped you.
If you have any questions, want to share a story of how our advice helped you or can help in any of the 3 areas I just listed, hit reply. I love hearing from everyone.
PS: If you’re tired of spending a lot of your time working on startup back office tasks instead of growing and working on your business, then sign up for a free call to learn how Chore can help you.