DESIGN LEADERSHIP

My 5 bitter lessons as a design manager

From handling user interfaces to handling people: Part I

Slava Shestopalov đŸ‡ș🇩
Design Bridges
Published in
11 min readJul 22, 2021

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Design leaders often grow out of yesterday’s designers. You are a designer with brilliant soft skills? Perhaps, you’ll be offered a leadership position someday. It has become common that heads of design, UX directors, and team leaders appear with minimal people management experience. That’s why we are destined to discover bits of this new skill set the hard way.

It’ll be fun, right?

1. You won’t be nice to everyone

One of my favorite sayings is, “If you want to hug the whole world, buy yourself a globe.” Before I became a manager, I had observed other managers’ work and believed I’d be much more humane, inspiring, and productive. I often caught myself thinking, “How dares he promote this specialist and give nothing to the other one? Why cannot we simplify this bureaucratic process? How come we hired such a person?”

But the reality is full of contradictions I haven’t been told about:

  • people who deserve recognition ≠ people who demand recognition;
  • highest-paid specialists ≠ top-performing specialists;
  • people who yell about their problems ≠ people who need urgent help;
  • likable team members ≠ people optimal for certain tasks;
  • things that are worth money ≠ unpleasant costs you have to cover;
  • processes convenient for designers ≠ company-wide processes.
Ideal solutions or sufficient resources are rather an exception in people management.

The world isn’t perfect, and a manager’s challenge is to do maximally right things within current limitations and be ready to sacrifice something if you do your best but still cannot satisfy all the needs.

For example, a choice between social justice and business:

Ahmed has been waiting for a deserved salary raise for half a year. He leads a local UX community; thus, contributes to our employer brand. Julie is the only knowledge-keeper for our top-performing product. She got a job offer from a competitor and demands a salary raise; otherwise, she’ll quit. Your budget suffices only one raise. What do you do?

Everyone knows how to become a better design manager except for actual managers.

One more example — retaining a team member:

You lead a team at a UX agency. Anna has the top salary for her competence level. She never goes the extra mile and doesn’t want to grow to the next position, so that we can increase her hourly rate for clients and have a margin for the next salary raise. Of course, you can let Anna go, but the job market is now overheated, and you remember that recruiters were filling the previous vacancy for two months. Your actions?

Whatever you decide in both situations described above, someone will certainly feel upset. I don’t want to sound like justifying bad decisions. I’m trying to say that people management is full of situations when there is no best solution, and you choose between “not great, not terrible,” “the least risky,” “good for now but a time bomb for later,” and so on.

2. “I’m alright,” often say unhappy people

A basic manager’s duty is to keep the team up and running. That’s why you regularly communicate with people and do your utmost to detect issues early. Sounds easy as pie: you talk, you solve, everyone’s happy, right? But like in user research, beware of taking words at face value.

Looking happy isn’t necessarily feeling happy.

Unless you are Dr. Lightman from the TV series “Lie to Me,” you’ll make lots of mistakes anyway. Checking up with people too often might annoy them and make them shut you out. If you don’t want to bother people, they should trust you to speak up in time. It’s hard to build trust from scratch, but it turns out even harder to earn trust if you replace the previous manager whom people loved. That’s a vicious circle!

While building trust deserves a separate article, I’d like to focus on its role. Trust enables a vital manager’s job, problem-solving. Once you break the ice, which is hard, you’ll see that the more people trust you, the more information they share. The more they share, the easier you cope with their concerns in the early stages. And the more problems you resolve for people, the more they trust you in return.

Understanding true people’s status is hard.

At first, I assumed the measure of my efficiency as a manager was problems I helped people with, but there are actually two strategies.

  • Reactive: “People don’t complain = I’m a good manager.” It’s similar to firefighting — a manager tries to discover issues as early as possible and fix them before the team spirit goes below zero. If people want something “above zero,” they should ask for it.
  • Proactive: “People are engaged = I’m a good manager.” A manager keeps the team spirit above zero by default and doesn’t let people have a spare minute for melancholy. Team members receive training, mentorship, pet projects, and new roles and generally become well-equipped for challenges, hence fewer reasons to complain.
These strategies reflect what state of team spirit a manager considers normal and aims at it.

Although both strategies are workable, I found the proactive one underrated. From my experience, if nothing bad happens, it doesn’t automatically mean that something good is going on. The phrase “I’m fine” today often means a delayed-action bomb for tomorrow. That’s why even in the absence of explicit complaints, I’ll double-check up with people who:

  • rarely interact in the team’s “Miscellaneous” or “Memes” chats;
  • skip many teambuilding activities in a row;
  • express no development goals or desired career directions;
  • haven’t spoken for a long time about their project;
  • don’t accept expensive bonuses from the firm (for example, a certification training course covered by our budget but with a note that a person has to stay in the firm for at least 1 year after passing), etc.
Behaviors speak louder than words.

One symptom might not mean anything serious, but multiple signs call into question the person’s “I’m okay.”

3. You are not their buddy anymore

Imagine someone installed self-made benches in your gloomy neighborhood. Such a skillful and generous person! And then this guy is elected deputy of the city council. From now on, citizens will suspect any of his charitable deeds, “Does that bench emit zombie rays or something? How much money has he laundered? What does he want from us?”

Sadly, it relates to design managers. A fancy official title might feel like a curse after you were an unofficial leader. Just a week ago, I was sitting with everyone, sipping coffee, and discussing stuff, but after promotion, my charm of the thought leader suddenly faded off. And now another person sets the team’s tone instead of me. So as you see, becoming a manager is gaining not just power but also new weaknesses.

The higher the title, the more responsibilities.

At the same time, responsibility grows larger. In the same way, modern designers aren’t just user advocates, design managers shouldn’t limit themselves to broadcasting employees’ whims. When a person is appointed manager, a firm doesn’t want to shoot itself in the foot and get yet another complainer. The whole idea of managers is to connect specialists with the business mission — not amplify the team’s anxiety.

However, serving business contradicts a natural desire of newbie managers to remain buddies for their yesterday’s peers — and now subordinates. Of course, I had the same temptation and used to see the new role as my teammates’ guardian. Just get me right: standing up for the team is vital; it’s just not the only possible behavior.

“Buddy” approach vs. “mediator” approach.

My mistake was positioning myself as part of the team; in reality, my place was somewhere between the team and business (or on the overlap of both). During my first hesitant steps in people management, I noticed that it was a real disaster when a manager loved their teammates and always took a stance against their firm and superiors.

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4. “Rockstars” are bliss, but also a trouble

When I met my first team, I was so happy to realize it included a couple of so-called high-potential employees (HiPos). Any book on people management will tell you these people are no less than superheroes:

  • require minimal supervision;
  • are reliable partners;
  • keep up the good work under pressure;
  • learn fast;
  • take on new functions easily.

A HiPo is the most desirable employee, so what’s the problem? While I won’t deny the bullet points above, there’s no rose without a thorn. As a newbie manager, I felt relief: “Phew, at least no need to babysit those guys
” And it led me to a dangerous conclusion I could relax and focus on the work with the remaining “normies” and “mourners.”

The one who cries draws all the attention.

But think about this: If you overfeed a pet hamster, it will get sick and eventually die; something similar happens to the most passionate members of your team. Self-motivated and self-organized people often overload themselves with new exciting initiatives, not realizing their velocity. Besides, as a manager, you are naturally inclined to plug up the holes with HiPos because they’ll never refuse or betray you. This makes top performers the first ones in a queue for — ta-da! — burnout.

(Photo borrowed from Alain Delorme’s series “Totems”)

Now imagine you lose a HiPo. A person who brings tons of value and inspires others can also do huge damage to the team. When others see a HiPo get demotivated or quit the company, they’ll start searching for new opportunities as well. It’s the “sausage effect.”

Let one person go “to a better place,” and others will follow.

Initially, I thought my work on a team was to develop the underdeveloped and calm down the dissatisfied. But I learned that all team members required attention, and here is a popular fable, which puts it perfectly:

One family bought a buckets of apples every week. There were always some apples that started rotting or were a bit bruised. So, the father took those apples, cut off the spoilt parts, and ate the fruit before they rotted completely. Eventually, he has not eaten a single tasty fresh apple for the whole time.

5. People won’t thank you for politics

I haven’t seen a single firm without office politics. Small studios suffer from favoritism and gossip; mid-size consultancies are torn apart by rivalry around who brings money to the table; siloed departments of corporations engage in trench warfare for budgets. So whether you want it or not, you’ll face some politics as a manager.

“The marvelous world of office politics” never features in manager job descriptions.

However, when I let a tolerable dose of politics into my professional life, I didn’t realize it was such an ungrateful thing. Literally, no one from the team will help you carry the burden of office politics — a maximum of one-two trustees if you are lucky enough. For example, let’s say you initiate a chain of escalations to defend against another department whose head tells lies about your team to the CEO. And you know what is likely to happen next? Soon people from your own team will get irritated and naively ask, “Cannot we all be friends? We are fed up with fights!”

Rephrasing a famous sarcastic billboard: “Office politics is like a penis. It’s fine to have one. It’s fine to be proud of it. But please don’t pull it out in front of your team.”

I supposed full transparency would make my team happier. It didn’t work out. Ordinary employees can digest only a tiny portion of the whole truth. I’ll think twice before ever openly speaking about:

  • internal rivals who are smiling at my subordinates but want to build their career with our team’s hands;
  • “royal court conspiracies”: who hates who and what “political parties” exist in middle and top management;
  • detailed information about staff utilization, turnover, and hourly rates;
  • real reasons why some people get what they get (tough compromises by the current or previous management), and so on.

Salaries is an example of managerial information that doesn’t make its bearer happy. Although knowing salaries is often essential to doing the manager’s job, your perception of people will never go back to normal. The next day you’ll see “price tags” above each team member and probably start comparing how much you like them with what they earn. Aargh!

People might want to know all that out of curiosity but will instantly regret it; this is controversial knowledge.

There are huge topics you can discuss only with other managers.

Having said that, every employee has the right to know about:

  • the company’s strategy,
  • the firm’s general status (profitability peak or crunch times),
  • career paths and self-development opportunities,
  • company and team news (achievements and failures), etc.

Please, get me right: office politics and conspiracies are crap; only maniacs take to it like a duck to water. The problem is that even good managers engage in politics and are doomed to receive no compassion from their teams. Otto von Bismarck perfectly put it, “The less you know about how sausages and laws are made, the better you sleep at night.”

In a nutshell

  1. Management is full of choices between “bad” and “catastrophic.” Many decisions may seem unfair unless you know the context.
  2. Team spirit is like a thermometer. It’s better to keep it high so that the team doesn’t plummet below zero when problems happen.
  3. Managers aren’t people’s buddies. They have as many expectations from their own teams as from the upper management.
  4. Even though rockstars on a team don’t complain and never let you down, it’s not the reason to leave them unattended. People who bring lots of value can also do lots of damage.
  5. Office politics is bad but inevitable, and no one will thank a manager for engaging in it even with good intentions.
The hardest lessons in my career
 so far.

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Slava Shestopalov đŸ‡ș🇩
Design Bridges

Design leader and somewhat of a travel blogger. Author of “Design Bridges” and “5 a.m. Magazine” · savelife.in.ua/en/donate-en