My time as an investor is really the first time I’ve ever worked with CEOs who weren’t formally (or at least, informally) trained as managers. My bosses all came up through the ranks. I went from Director to VP to Founder to CEO. Most of my SaaS CEO peers, back in the day, had management experience under their belt.
It’s fine. You can learn this stuff, and all that really matters is attracting a great team under you. Really, that’s all that matters post-Initial Traction.
But if you come up through the ranks — you at least get to observe how others do it. If you skip past all this, you may have missed seeing some basic stuff in practice that just helps.
So if you haven’t hired and managed managers before, my learning is that a few simple-ish processes can make being a Better Manager as simple as pie.
Here are my top suggestions:
- Have unstructured weekly, or at least biweekly, 1-on-1s with all your VPs. So many folks just don’t do this. The key is to have no deep agenda, that it not be a performance review. It’s the opposite. It’s a chance for each VP to raise thoughts on his or her mind, without structure or boundaries. To brainstorm. To get help. To show off. To get some love from Mom or Dad. Whatever it is. It can be a 20 minute meeting. But you gotta do this. More here.
- Then, try to get your VPs to have 1-on-1s with each other. Your VP of Sales and VP of Marketing need their own 1-on-1. If they haven’t done this before, get them to. Same with VP of Product and Engineering. Sales and Customer Success, etc. Yes — they work together Every Single Day. But that’s not the same thing. >> Offer to pick up the tab for lunch or dinners here. <<
- Have weekly staff meetings. Yes, you need to do this. Every week, the management team gets together for 30-45 minutes and just updates everyone on what they are working on. I know you Slack and email. But this forces you to do it together. As CEO, have a really basic agenda for this one (unlike 1-on-1s) … but really basic. And no, daily standups are not a replacement for getting your management team together once a week for a deeper dive. More here.
- Have a core set of goals and KPIs everyone always uses and tracks to. That don’t constantly change! Start with your ARR goals for the year. Make sure everyone in the company knows your Top 5 Goals. That they’re reviewed at every company meeting. Every team meeting. Every board meeting. One set of goals, that can be judged. And update them every time you are together.
- Have Your VPs Present — and Present More Than You — at Board Meetings. Ok, board meetings in the early-ish days can seem like a bit of a tax. Don’t let them be. Use them as a vehicle to push the team. Make sure each board meeting has sections for every functional area — and have the owner present, not you. Your board members talk to you enough. They don’t hear from your team enough. From them, they’ll learn a lot. And even more importantly, it will create external accountability for your VPs. They’ll know they have to be accountable not just to you, but to the board too. This really works. So — as CEO — talk less in board meetings. And try to barely talk at all in the functional areas of your VPs. More here.
- Recycle your Board Meeting Presentations as Company Meetings. Transparency builds trust. Take your board meeting materials, make a few edits, and then do it again in front of the whole company. Your VPs won’t have to do much extra work this way. The employees get more info than they’d otherwise … and they’ll feel like the insiders they are and should be.
- Celebrate. Now that I’ve worked with several start-ups that have gone from nothing to $5m, then $10m ARR, and beyond — HEY WHERE WERE THE PARTIES? You gotta celebrate, and spend some coin. Do it nice. Your team and employees may not remember a 2.34% bonus. But they will remember that amazing retreat you went on. That crazy outing. Do it. And not on the cheap. Together. And make them feel special. They are. A bit more here.
Most first-time CEOs I work with do almost none of these 7 suggestions.
They each are relatively trivial to implement. And I bet they’ll have an outsized impact on communication and morale across the team. And make you a better CEO — almost overnight.
And finally, let me add one uber suggestion, which really should be #1: Build a More Diverse Team now. This just has so many benefits. A more diverse team is less fragile. A more diverse team is more welcoming to a variety of ideas. A more diverse team, in my experience at least, is less likely to quit when the going gets tough. A more diverse team makes hiring easier, as more folks will feel comfortable working at your start-up. More backgrounds, more ages, more experiences, more countries, more inclusive. It just works. It pays dividends.
“Unleashing Success: Celebrating Big Wins Together!” with Cloudflare's CRO
— SaaStr (@saastr) August 22, 2023
image from here
(note: an updated SaaStr Classic post)