There may be nothing I’ve seen wreck the careers of high-performing, hardworking people more commonly than stepping into a manager role the person isn’t ready for. At the same time, great people often seek stretch roles. So how do you know if you’re ready? >>
The pattern of seeking stretch roles fast happens often at startups. Your startup may or may not turn $$$, but the thing startups give you compared to BigCo is the chance to catapult your growth ahead several steps. You get to do things you're not qualified for on paper.
Sometimes this works out great. I can think of numerous times I’ve promoted someone into a stretch role (either internally, or hiring someone externally into the stretch role) where the bet has more than paid off.
However, I’ve also messed this up several times in my career: seeing someone’s delivery and work ethic, believing in them, and asking them to lead teams when they lack the foundation. (It’s my fault when this doesn’t work out well rather than the person I’ve promoted.)
Having experienced cases that have worked out great and cases that haven’t, here are four ways to assess if you're ready for a manager role.
First, can you communicate complex expectations clearly? Inexperienced managers often assume management is all coaching and mentoring. That’s part of it, but coaching only helps someone if it happens in a context where it’s clear what “good” looks like.
Not communicating clear expectations and holding people accountable to them is the biggest mistake most managers make. And when you fail to communicate clear expectations, people usually disappoint you. When this happens, it’s nearly always the manager’s fault.
Second, are you comfortable engaging in and managing conflict well? Optimizing to avoid conflict is the second biggest mistake that most managers make. This happens when the manager’s primary focus is on being liked rather than being fair.
Done well, management is a high-conflict job! It’s emotionally exhausting. Most managers way underestimate this and avoid this aspect of their roles. So make sure you have a comfortable track record of engaging in productive conflict.
(This doesn’t mean you get to approach conflict with hostility, though. You need to engage with conflict with poise and maturity to be ready for management.)
Third, do you typically get things done by being a hero, or do you build predictable and accountable systems to deliver you goals? Are they methodical systems that you proactively share and build with others?
As an IC, hero work can be super effective. But as a manager, it’s usually terrible. Managers mostly do hero work to compensate when their team isn’t delivering.
BUT! when the team isn’t delivering, that’s usually because 1. The expectations weren’t clear, 2. The system wasn’t designed to support effective delivery, or 3. The manager never gave clear feedback.
In other words, as a manager, hero work is usually your last recourse when you’re trying to overcompensate for your prior management misses.
Finally, do you have the right technical/functional foundation to credibly lead in all of the above ways? It’s always easier to promote someone with this background because they start out with credibility with their new team.
To design the right system, set the right expectations, and engage with the right conflicts, it just deeply helps to have had the reps in someone else’s system(s) to learn what good looks like.
So now when someone says they want to develop their career as a manager, I tell them that I’m looking for:
- Ability to set clear expectations
- Ability to engage and manage conflict well
- Ability to build systems vs defaulting to hero work
- Technical/functional foundation
Paradoxically, the higher-performing you have been, the more important it is to make sure you are solid on the above before taking the leap.
Stepping into a role you’re not ready for sets you up to fail short term and can be incredibly damaging to you confidence in the medium-term at least. It can take you years to recover.
So in a nutshell, make sure you’re ready for it before you accept that manager role! There's no grand prize for failing fast, especially when you're taking responsibility for other people's development. You got this 🌠📈🚀
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I don’t know very many people in tech who aren’t feeling tired right now. True at every organization and seniority level.
And yet, objectively speaking, people in tech have had it comparatively way better than most people since Mar 2020. So what’s that tiredness about? >>
Let’s start with some stress factors in tech:
- Covid
- Culture tension over DEI: Progressive workers having expectations that orgs usually haven’t met
- Culture tension over WFH/in-office
- Market drop and job threat
To name the obvious, those factors ARE really stressful for everyone involved. The last few years have been a uniquely challenging time to work and lead, certainly in my professional lifetime.
Today would've been my grandma's birthday. She died 13 years ago, a couple of weeks before my kid was born. She was quite a lady. >>
She finished at the top of her high school class, with special distinction in math and chemistry. But she wasn't allowed to go to college. That was for her brothers.
She channeled her considerable intellect in two ways: Raising her five children and rabble-rousing.
She famously took on our town water department when she discovered they were systematically overcharging older people — and, with no legal training, she won.
As a leader, there may be no skill more important than emotional self-regulation. I struggled with this for a lot of my career (which of course as a woman, made me extra worried about being a trope). Thread >>
First, a leader’s job is to bring calmness and stability to chaotic situations. For everything you say, you have to ask: Am I making this better right now or making it worse?
You can't just say everything that crosses your mind. It took me a long time to learn this. I’m a transparent person. But transparency isn’t the same as unfiltered emotion. It’s scary to be on the receiving end of unfiltered emotion from your boss.
I have been managing people off and on for a long time now. Here are 10 open, vulnerable, painful mistakes I’ve made. Ouch. I’m sharing them so you don’t have to make them too. Thread >>
1/ Shying away from giving difficult feedback. This is my top Grade A mistake. It’s always easier to not give tough feedback in the moment, to let the moment pass. This is a dangerous habit. The immediate issue might pass, but the broader issue recurs until it becomes unbearable.
Management is not a job for the conflict-averse. Do your job. Give difficult feedback early before it multiplies!
I started my software career as PM at Microsoft. When I took the job, I expected to do it for about a year while I figured out what I wanted to do next. Here are 9 things I learned there that both surprised me and helped me in the long term. Thread >>>
1 I had never heard of PM as a job before being one. But it turns out the stuff I'd done before, the roles I’d had in school projects, in volunteer activities, etc — I was just a PM without the title. You don’t always have to be qualified on paper to be able to do a job.
(Fun fact: I had initially interviewed at Microsoft for a totally different role and, based on how I did, got asked to re-interview for a PM job instead. The recruiter who saw the whole process and advocated for me changed my life! Recruiters are magic.)
1 Whether you're brand-new to management or highly experienced, here are 10 questions that you need to get great at asking, and the situations where you need to ask them. Thread >>
2 When someone is feeling overwhelmed: What 3 things must happen in the next few months for everything else to succeed?
(Help them cut / deprioritize everything that isn't those 3 things)
3 When someone is struggling with a teammate: How would your teammate explain what is going on?
(Help them see it from the other's POV, develop healthy self-criticism)