Top reflection after 24 1:1’s in 40 hours

Wil Reynolds
4 min readOct 25, 2019

I just had 24 1:1’s (ish, a few were 2:1’s) in 40 hours, one reflection regarding moving up in an organization or laterally to a new challenge (also a promotion in my eyes) is this…

Crystal (not me) having a 1:1 in our SD office, this was just a better picture :)

If you want a promotion, consider not talking about it.

Your manager isn’t waking up saying, “who should I promote today?” or “I’mma go promote me some peeps”.
Your manager instead is saying:
Last quarter was ROUGH, who are the people on my team who solved a LOT of problems for me?
Who helped me to see things that I didn’t see, proposed solutions, saw it through, whom couldn’t I live without?
Who might have been able to help me tackle some of those problems?
Who handled shit on their own while I was OOTO on vacation and crushed it, maybe even doing it better than me?
I want a promotion, who could back fill MY roles when I go to make my pitch for a promotion?
Who is connected to our team’s / company’s vision? I wanna keep them, let me think about promoting those people.

Talk about the problems you want to solve, that if you solve them are highly likely to put you in a position to get you that promotion.

Before you start, ask a BETTER QUESTION, saying I want to get promoted, doesn’t help you get any more information on HOW to get promoted.

Ask for the toughest feedback.
Ask: Do you see me as someone who can see something through?
Ask: Do you see me as a high performer? Why? Why not?
Ask: What about my working style is most likely to self-sabotage me on this journey?
Ask: You’ve seen 100s of people ask for promotions, what do most people get wrong in their approach, am I doing that?
Ask: What’s most frustrating for you when someone indicates they would like a promotion?
Ask: Think back to your last 3 promotions, what are the common threads about those three instances / people?

Find out what problems to solve:

Do a “skip level” and ask your managers/manager this question:
Ask: “What is something that you / your managers just don’t have the time to get done?”
Ask :“What is the value to you of solving that?”
Think: “Are those problems I want to solve?”

Create a cadence of accountability:

Say: I intend to (love this language) create a doc that I’ll share my progress on that. (hint here’s one I built, part of a longer post, and it works well). 4DX was instrumental in helping me think about cadence of accountability & lead measures (below).

Ask: What leading indicators would tell you that we’re on the right path?
Ask: When I hit roadblocks might you be able to make time to hear me out, advise me, or connect me with others who can help?

Talk about a plan B in advance:

Sometimes, the timing SUCKS and you’ve been working your plan, doing all the right things, and the company / your manager can’t promote you. This is an opportunity to ask a better question.

Ask: If I hit these goals and for some reason you can’t get the promotion approved, what can you commit to doing to help me / reward me?
Ask: If this promotion is about money (and that is OK), you can ask, can I get bonused at that level even if I can’t immediately get the title?
Ask: Will this role be filled before my timeframe? If it is how quickly might we be hiring another?
Say: If I don’t get this promotion, I’m going to / not going to quit in 6 months, 12 months, etc.

Let your manager know (and dig deep to understand) why this promotion is important to you. Is it internal prestige, is it money, is it to earn respect, is it to have more authority? The more you dig into your “why” the better off you are in articulating plan B’s in case it can’t happen.

I’ve promoted several people who came to me saying they wanted a promotion too, my style has been to follow the above, do whatever works for YOU!

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Wil Reynolds

Serial Underdog @seerinteractive doing SEO, Marketing, & Stuff, I am whatever you say I am.