- Overstating your case
- Keeping your mouth shut
- Arguments don’t kill releases, people do
- Dress for the job you want
- All certainty is false
I learned long ago never to wrestle with a pig. You get dirty and besides the pig likes it.
– G. B. Shaw (misattributed)
That’s all well and good except I’m pretty senior now. Suddenly part of my job is winning arguments.
As beginning managers we sometimes luck into getting angry about the right thing, and insist on it, but are reluctant to assert ourselves with a cool head.
This caution doesn’t serve your career or the interests of your team.
Overstating your case
Unless your middle name is XIV and your first name is Louis, the first kind of managing you do is managing up – the art of doing unto other before others can do unto you. And even the Sun King had to contend with an overbearing regency in his youth.
In trying to justify new projects, score choice assignments, or avoid hard conversations, I’ve been guilty of saying things like:
- This won’t take a month – it won’t even take a week
- We’re in the home stretch
- Y is definitely better than X and won’t introduce new problems
All of these are famous last words in my career. Deadlines slip and I feel guilty about basically lying to get my way.
But the worst outcome would be loss of trust of my manager, and that happens less than you’d expect. I think there are some sound reasons for this:
- I’m not exaggerating to serve myself, I’m doing it to keep the project on track (albeit unsuccessfully)
- Things are already off the rails, and everyone’s bad at estimation there
- People weigh advice – a smart manager won’t blame you entirely for leading them astray
Guilt over being wrong has made me cautious to ever express certainty. But these days my judgment is (a) better and (b) a job requirement. There’s a healthy version of certainty that is a necessary ingredient of assigning good work and getting it out the door. And it’s okay to be wrong some of the time.
The ‘right’ amount of certainty is a calibration that changes per person and per job. But it’s implied in every conversation that you’re not 100% certain. When you go further and tag a claim or plan as ‘not sure about this’, you’re not going from 100% to 50 – you’re going from 40% to 10.
Never expressing certainty is the same as never engaging in argument, and every project has an argument at its core – about long term plans, about short-term work that puts us on that track. Difficult conversations uncover the holes and fill them in. Without argument you’re choosing plans at random.
Keeping your mouth shut
If must fight … win
– The 80s
A few years ago my first thing at a new job was to speed up a slow batch job. I tinkered for a week and finally brought my team a solution with like 100 lines of C++ on top of the python codebase we had before. As a POC it was a success – it ran in hours instead of days.
My manager nixed it, and so I ditched the C++, tinkered for another week, and then brought him a finished solution with C++ re-added. Was it the only way? Not sure, but it worked.
He was angry but not that angry. I still felt guilty about working around him. For the rest of my time at that job, I tried to work with him instead of challenging his assumptions. I was bad at it – it’s hard to know what people’s assumptions are. And for the whole time I was in ‘don’t fight’ mode, I got nothing else done at that job.
Over time, at other jobs, this got worse. I stopped challenging bad information. I became terrified of people who say things that are obviously wrong, because I didn’t know how to call them on it. I made it my point to be polite, patient and not interrupt. But wrong arguments can get pretty long-winded.
It’s risky to take a minority opinion when you’re outnumbered, and tiring when you turn out to be right and can’t use ‘I told you so’ to win the next argument. I thought it would be easier to go with the flow. I thought that people maybe weren’t as wrong as they seemed and their plan would be as good as mine.
WRONG. When your spider sense is tingling, you have to surface it. And it’s exhausting to internalize other people’s side of a fight, which you do when you work on a bad plan.
Ultimately you’re keeping your mouth shut because of a thesis, either spoken out loud by your org or implied, that skill & judgment can be separate and dwell in different people. But that’s seldom true. The implementers need to be in the room for design, arguing loudly for their priorities, or the plan we go with will be insane (technically speaking).
Arguments don’t kill releases, people do
A work is never completed except by some accident such as weariness, satisfaction, the need to deliver, or death.
– P. Valéry
I’m always on eggshells about throwing shade on a plan near its deadline. I don’t want my doubts to hurt the release date. But an even slower way to uncover problems than argument is implementation.
I asked three different friends about arguments and got the same answer: every new idea is badly received. As a leader it’s your job to bring people along with you.
‘No doesn’t mean stop asking’ sounds like tricky JT Doggzone dating advice, but apparently is an optimal starting point when persuading colleagues.
I’m wondering if part of my caution about picking fights comes from picking fights with the wrong people. By which I mean people who:
- Think that every detail of their original plan must be preserved in stone
- Would rather debate endlessly than compromise
- Reveal surprise changes between design & release. Sometimes this is necessary but in general it’s a lack of discipline, a workaround to the design process
- Don’t know their reasoning because they internalized someone else’s opinion, and now are blindly arguing for it in a wider setting. In a Julian Jaynes ‘voices in your head’ kind of way, this is insane. I’ve been crazy this way and it’s not fun.
- Worst of all: people not willing to engage in any argument at all. People who can’t defend their plan without getting angry, but also the ones who can’t help you unravel a problem or bounce ideas.
Even healthy people can APPEAR to have these bad traits when you’re not holding up your end by fighting for your beliefs, i.e. your skills and organizational knowledge, i.e. your spider-sense.
By opposing all argument, these characters are also the enemy of finishing. But by not fighting them with the right tools, you’re the enemy of finishing too. It’s like the Gita. If you let them pull the bus over you’re just as bad, because you shouldn’t be a passenger. The goal of argument is to release something reasonable, not to design something perfect.
Dress for the job you want
Hegel remarks somewhere that all great world-historic facts and personages appear, so to speak, twice. He forgot to add: the first time as tragedy, the second time as farce.
– K. Marx
I think I’ve had every job twice – once in a shitty, not-ready kind of way. Then I high-tail it out of there, get another similar job, and having learned from my expensive failures at the previous shop I can contribute competently to what’s going down.
(We should do more to retain people who have received expensive training. That’s a different blogpost).
My point is that the interview is a place where expressing false confidence is socially acceptable, where overselling is encouraged and expected. The key line in an interview is often just one sentence, a ‘have you done much X’ or ‘how will you help us Y’. It’s often not tested, not even with a ‘conversational background check’, because it takes a lot of brains and experience for the interviewer to ask the right questions. You might call these argument skills.
This ‘expected oversell’ dynamic in the interview should be the norm in design meetings too. Expect people to make claims of varying validity, make it normal to dig down and question.
The ‘month of birth bias’ stuff in Outliers is interesting to people because it gets to fairness. This is the effect where older children in an academic grade win at sports because they’re larger and more developed. Impostor syndrome is interesting for the same reason – people of equivalent ‘potential’ or ‘ability’ do less well because they’re not heard or don’t speak up. In both cases teams may benefit from digging more to identify our best performers.
I mention these in the same breath because they’re not opposites, just sides of the same coin – phenomena that confuse people’s capabilities and obscure the truth. Certainty is the same way, but you as a senior IC or new manager can control that, dialing it up or down to serve your team.
All certainty is false
There’s a Terry Pratchett line about how people believe in the supernatural but nobody believes in chairs.
Certainty, like faith, is only brought to bear after reasonable people have disagreed. Don’t be afraid of ‘false certainty’. If you had access to objective facts, you wouldn’t need to bring certainty into the argument. Certainty is a tool for situations where you don’t know the facts, where you need to weigh your judgment.
If your emotions are causing you to not speak up because you may be wrong, they’re serving you badly. If the other people in the room are 100% sure, they’ll say so. Otherwise, follow your instincts. Fight the good fight.
Good orgs will judge you more harshly for not betting than for betting wrong.