One privilege I get as part of mentoring and investing in a few dozen startups is a chance to work with first-time managers.  The reality is, most start-ups are better off with a Stretch VP than a Never Did It But Has a Great LinkedIn VP.  More on that here.

And as part of that, I see a lot of ambitious, driven first-time managers screw it up. 🙂  I thought I’d share 7 actionable tips to help you if you’re getting your first big shot now …

  1. Make a firm rule: No Excuses.  This is probably the rookie error most first-time managers make, and many second and third-timers as well.  Excuses actually work fairly well in Big Companies, because it’s often not exactly clear who is responsible for many things in large organizations.  But the #1 reason a VP is hired in a start-up is to be an owner.  As part of an owner comes the rule of No Excuses.  Missed the quarter?  Just tell me why.  Made a few wrong hires?  We all have.  Just tell me the action plan.  Etc.  Never make excuses.  Instead, simply identify challenges and mistakes as early as possible, and just come up with an action plan.
  2. Get a Formal Mentor.  We all need mentors, but especially, first-time managers.  Tell your CEO or boss that you need one.  And founders — reserve some shares and a few dollars to mentor your stretch VPs back.  Maybe reserve 10% of their salary and/or 2%-5% of their option grant for their mentor.  And if they don’t know a good one?  Go find one for them.  Or use a tool like to help you, e.g. for your engineering leaders.
  3. Do Weekly 1-on-1s.  Force your boss to do one with you (nicely) if she/he doesn’t do them.  An unstructured, weekly 1-on-1 is one of the best ways to collaborate, raise concerns — and build trust.  More on that here.
  4. Ask for Help.  This is #4 on our list, but probably the most common mistake.  You are not hired as a first-time VP or manager to know everything.  No one expects you to.  But they do expect you to ask for help when you need it.  Not on everything, but even as often as once a week.  Asking for help is not a sign of weakness.  It’s a sign of self-awareness.
  5. Understand Your Boss Likely Isn’t Perfect.  First-time managers often have idealistic expectations of their bosses.  Often, their bosses haven’t done it either.  Don’t let this frustrate you.  Instead, focus on the fact that she hired you and believed in you.  And remember, if you haven’t worked directly for a founder before, that they are … different.  More driven.  Hopefully, more appreciative.  More enabling.  But … different.  You’ll have to evolve.
  6. Learn to Thrive on Criticism.  This is hard for all of us, this author included.  But the best managers thrive on criticism.  The 5:1 / 10:1 rule (5-10 pieces of positivity for every 1 piece of criticism) is a good golden rule for line management.  But as a leader, ask for more feedback.  Criticism with a caustic bent is never truly helpful.  But the more senior you get, the fewer pats on the back you’re going to get when you ask for feedback.  Learning the 5 things you could have done better last quarter?  Tough to hear perhaps, but also priceless if you can find a way to not take it personally.
  7. Understand the Rules on Being Topped.  This is one I was never great at, but as a first-time manager, ask how long you get until you are “topped”, e.g. until a VP or SVP or CRO or whomever might be brought in above you.  Sometimes, your boss may not know.  But I’ve learned having an honest conversation here, if you can, is better than not knowing.

Plus a Bonus 8th Tip, probably the most important:

8. Transparency is Your Top Ally.  Don’t hide from anything.  Don’t hide from bad news or mistakes.  Don’t hide from a tough quarter.  Instead, share as much as you can, dispassionately, again with action plans.  However you do it, remain confident but share.  Transparency always builds trust.  Everyone knows this, but sometimes, first-time managers retreat here a bit when times aren’t perfect.  That’s the time to share more, in fact.

And finally … once you finally have it figured out …

9.  Don’t Be Scared to Hire People More Experienced Than You.  Do it.  Eventually, if things work, well the only way you’ll scale as a first-time manager is if you get comfortable and confident hiring people more experienced than you.  As a Stretch VP of Sales, for example, it might be fine for your first sales manager to be less experienced than you.  But what about 6-12 months later?  When you need to hire 50 reps?  You’re going to need to hire another VP of Sales under you.  And someone that has hired far more people than you ever have.  Embrace it.  Don’t be scared of it, or run from it.  The only way you’ll grow from a Stretch VP in Year 1 to a Great VP in Year 5 is if you learn to hire people more experienced than you, as managers, under you.  They aren’t threats.  They are how you scale.

Whatever you do, realize as a Stretch VP, your boss knows.  She knows you’re a stretch.  She isn’t expecting the impossible.  She isn’t expecting you to know it all.  What she/he is expecting is that the organization is in a better place than before you joined, and that she knows and can trust you’ll keep getting your piece of it to the next level.

Dear SaaStr: I Think My Boss is Going to Hire a VP Above Me. What Should I Do?

(note: an updated SaaStr Classic post)

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