Here’s my list of the best golden advice I was given as a first-time — and second-time — CEO:
- Manage People — In General, and Earlier. The earlier in your career you can learn how to manage people, the faster you can excel in learning to scale. Managing people isn’t always fun. But embrace it if you want to be a CEO, a founder, and/or be a part of something bigger.
- Listen to “Audibles” and Act on Them. Your best bosses, VPs, mentors and others will give you “audibles” — quick bits of micro-advice during pitches, customer meetings, interviews, etc. While you are in the process of working 🙂 They’ll see where you could improve in real-time. Take this real-time feedback and leverage it and act on it immediately. If someone else great is in the room with you, these audibles can make the difference between a positive outcome and a negative one.
- Celebrate Your Wins. This is tough to do right for most of us. There’s always the next quarter, the next milestone. But you have to truly celebrate the wins. Especially as founders, we tend to go heads-down after a win, because it’s just one step in a bigger plan. But the team needs to celebrate the wins, and maybe you do, too.
- Spend 20%+ of Your Time Recruiting. Recruiting isn’t fun. But nothing is more important once you have something. Force yourself to spend 20% of your time doing it. If you aren’t investing 20% of your time, you’re doing less important things with that time.
- Get on a Jet. Often. Go visit your customers, partners, and prospects. Relationships aren’t built on the phone or on a Skype. Or at least, only superficial ones are. If you are going long, you gotta show up for the important ones.
- Slow Down the Biggest Decisions. Speed Up All Other Decisions. Actually, I never got this golden advice but needed it. Big decisions — slow them down. If you are risking the company, it almost always can wait a week. Get more advice. Sleep on it. Mull it over. But everything else? Push those decisions down and move faster. As long as you can fix any resulting mistakes later.
- There Are Only a Handful Of Great Co-Founders and VPs. Go All In on Them. You will interview 100s and then 1000s of folks over your career, and hire many very good, pretty good, OK and less-than-great folks. But just a handful will truly be able to move the needle for you. Go all-in. Let their weakness go, and backfill them. Support them when they make mistakes. Let them grow and hire and scale as far as humanly possible. Only a few will truly make a huge difference. Hire them immediately, over-compensate them with equity, appreciate them … and most importantly, get out of their way. Let them run.
Plus let me add some of the best tactical advice I was given. Those ones aren’t the “7 Best” overall — but they were some of the most impactful tactical advice that truly helped me:
- Hire someone full-time ASAP to manage your “big” customers — once you have even just 1-2 of them. As CEO, once you close a few big customers, you can’t manage them yourself. Yes, the customers will always want to talk to the CEO. But you don’t have enough time to make them happy and successful. As soon as you close your first “whale”, hire someone full-time to make them happy.
- You can go further than you think. For many of us, a time or two will come when we secretly want to throw in the towel. And in fact, we often come close. Maybe you should. Maybe it’s time to hire someone else to replace you. Who knows. But one thing is usually clear … if you can get the company to 10, 100, 1000 customers … you can go further. You can find a way. As a founder, you have this special knowledge of how it all comes together, why all the pieces work (and don’t work), and what the future will bring. You can go further.
- It’s OK to take a quarter to rebuild. Yes, startups have to grow or die. But transitions are tough. Building the second management team, going upmarket, breaking through technical debt. Sometimes, you need a quarter to rebuild and let the pressure off for growth that quarter. You can’t do this often. But it’s worth letting the growth pressure off a few times on the way to $100m in ARR — to focus on fixing management team, product and other debt. They are like mini-sabbaticals where the team can focus on rebuilding and fixing things and not just “crushing” the plan.
- Your best mentors will give you advice that hurts. Most folks will not give you tough advice, and even more importantly, they won’t know you and your business well enough to give the really tough advice. The advice that hurts — because it’s right, and it points out where you should and can be doing better. You may be tempted to pull away from the mentors and advisors that give you advice that hurts. It’s natural. It’s hard enough to just keep the engine going. But keep and maintain those relationships. When I look back, that was the advice that really made a difference. The advice that hurt.
- Sometimes, you really aren’t ready yet. I always pushed hard. To go upmarket. To close every logo. To push out every product, every release. And indeed, I do think that 8.5 times out of 10, that’s the right thing to do. Perfection is the enemy of progress. A Good Plan Today is Better than a Perfect Plan Tomorrow, etc. Ask for forgiveness, not permission. Yes — but not always. You need to learn judgement on when to pull back. When a bad release isn’t worth it. When maybe, somehow, you have to let that amazing potential customer go … to a competitor. Not usually. But you can’t take on every battle. Maybe, retreat 10-15% of the time. Not forever. Just for now.