Your #1 Management Hack: Weekly 1-on-1s #SmallBiz - The Entrepreneurial Way with A.I.

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Saturday, July 11, 2020

Your #1 Management Hack: Weekly 1-on-1s #SmallBiz



When I catch up with founders on the march from $1m to $10m in ARR, the number one topic has always shifted to recruiting.  Where do i find a great VP of Sales, Marketing, Engineering, Product, Customer Success, etc.?

Sometimes, it seems like simply building a management team is all you have time for.  But it’s not.  It can’t be.  It has to just be the start of a journey together.

Once you finally build out your first management team, the last thing you want to do is lose it.  Or more subtly, for your team not to perform as well as they could.

The question I always ask founders here is:  Do you do regular, scheduled 1-on-1s with your VPs and direct reports?  I’d guess 90% do not.  

Most of us end up with once a week staff meetings.  That’s OK.  But it’s not a substitute for a 1-on-1 with your VPs.

Ultimately, I’d suggest the following cadence:

  • Daily meetings with your co-founder.  A quick catch up, if you are both in town.  If you guys don’t want to do this — that’s a sign of trouble.  I did this every single day with my co-founder of my first start-up.  It was a highlight of every day for both of us.  We just got together at 6pm every day, and talked for 15 minutes about our days.
  • Weekly staff meetings with your entire team.  This meeting should have an agenda, and should be about 60 minutes max.  Note that meeting is not about you.  You should already know most of what your team presents.  Rather, it’s a forcing function to get the team together and share information, especially cross-functional information.  And to make sure folks are working together than need to be.  So your VPs don’t end up in silos.  Review your goals for the month and quarter, and status updates from each functional area.
  • Monthly all-hands company meetings.  Most CEOs do this, but not all. At least once or twice a quarter, and ideally monthly in the earlier days, get everyone together for an all-hands meeting.  One hack: just use the board package from the last board meeting as the template for your all-hands meeting.  At least, 90% of it.  It’s usually a great set of slides for you and your VPs to present from, that everyone has already put a ton of work into … without having to do a lot of new work.  After all, you already presented your board slides just a week or two ago before.

and … and this is the tough one:

  • Weekly or bi-weekly meetings with all your direct reports.  I know you are busy.  I know if you have 5 VPs, the last thing you want is 5 more scheduled meetings a week.  How can you even possibly fit them in?

You don’t have time for 1-on-1s.  This is true.  The thing is, you also don’t not have time.  There isn’t a better investment you can make in your VPs than meeting either once a week, or at least, once every 2 weeks.  Get it on the calendar.  And probably, have it agenda-free.  Some folks like to have agendas for 1-on-1s.  But I find them more valuable to talk about whatever is on your VP’s mind.  Not what she has to get through at each weekly staff meetings.  So that you can help.  So that you can backfill areas she needs help.  Or even just so you can help be her work psychiatrist 🙂

If you are like me, you can’t stand too many ‘standing’ meetings. But you have to do them this way.  So one hack is to package them back-to-back with other scheduled meetings.  Do one right after your weekly staff meeting.  One right after a team lunch.  One right before something else.   One over a libation on Fridays at 5pm.

Chatting in the hallway is not a substitute.  Talking in a team format at staff meetings is not a substitute.  Even talking during customer pitches or scrums is not a substitute.

It’s 15-20 quiet minutes, 1-on-1 with each of your reports.

Every week or with some, every two.

Do this, and management will get easier, the team will trust you and each other more, and you’ll execute faster.  With less need for anyone to look over their shoulder, worry where they stand, or even if they are doing a good job.

(A 2020 update of a classic saastr post)

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