Bonnie Siegler | Dear Bonnie

Dear Bonnie

Dear Readers,

Last week I asked you to submit advice for me and, of course, other bosses. Specifically, I wanted to know the answer to this question: What's the one thing you wish your boss did differently? 

And you answered. 

I have compiled and combined your responses below based on their themes. If you see your boss in any of these examples, maybe you can casually suggest they check out Design Observer. If you see yourself in any of these examples, you should, ya’ know, maybe, possibly, what’s the word? … Change.

I wish my boss would learn how to make requests more appropriately, in a way that will make me want to do what he's asking. His approach when he asks you to do something is to send a very blunt email: "This is horrible, change it," or "Nobody likes this, make it different." I have a feeling he doesn't mean them to come off as harsh commands, but they do.


I work on many projects at once and I have a hard time prioritizing without clear deadlines. The work I do is not time sensitive, so there are rarely strict deadlines, but I always like it when my boss gives me dates when she would like certain projects finished, which she doesn't do very often.


My boss' directives or wishes get lost in translation between her and the other two heads, which results in me getting very mixed messages regarding my assignments. If she were firmer about executing her vision and not compromising, things would be much easier for me and also much better for the company.

I often get emails about tiny details that my boss really shouldn't be focusing on, and hasn't focused on, and won't focus on in the future. However, he has a tendency to laser in on these little things as a kind of productive procrastination, instead of devoting his attention to the bigger issues.


Sometimes I think my boss likes my job more than his. He wants to be an individual contributor with minions, but we need him to be so much more than that.

My boss is incredibly stingy about vacation time. We accrue it based on how long we've been working there (so people often have fractions of days), and it's entirely non-sensical. And on top of the weird policy, my boss doesn't value vacation time at all, and rolls his eyes and sighs when anyone asks to take off a few days even if they haven't taken off time in months.


This might be one of those "be careful what you wish for" situations, but I would love to know what I am doing well and where I need improvement. I need to a) know what my boss sees as my strengths and weaknesses and b) have them give me concrete feedback based on what those are. She also needs to be upfront about any potentially “difficult” issues that need to be discussed. We are always in the dark about our performance. Currently, I have one review a year. It's a vague meeting that is basically a pat on the back. It would be nice to have a peer-to-peer review, a review from my boss and a review from a direct report.


My boss rarely stops and asks us to review projects as a team. Sitting down for thirty minutes to an hour after a project is completed to go over what went well and what went wrong would help resolve some of the recurring issues. It's impossible to improve processes when we move so rapidly through projects and timelines and don’t ever learn from mistakes because they are never acknowledged.

I have worked at a big company for over two years and I think I've had a real conversation (about work or otherwise) with my boss maybe three times. She is completely uninvolved, and it is one of the most demotivating experiences I've ever had; even if there is no room for growth in my particular position, feeling valued in even the tiniest way as a person rather than a process would be extremely helpful. Since that's not likely to happen, I'm probably going to quit soon.

And many of you also pointed out some good boss traits, along with the bad ones. Among others, you mentioned your boss being willing to change his or her mind, wanting to hear your opinions, being supportive and encouraging, caring and considerate, friendly and generous, and being especially good at making employees feel valued. We all carry good traits along with our bad, but here’s the thing: every single complaint above, which all interfere with work performance, whether through bad feelings or an actual work inhibitor, are eminently solvable in about five seconds. 

Be nicer? Start every email with a nice word. THEN jump in with the truth.
Deadlines? Set one.
Take more control? Ask your employees if they are clear about what they are doing.
Focus? Focus.
Do your job? Do your job.
Partial vacation days? Change that silly policy.
Feedback? Give it.
Team reviews? Do them.
And do talk to your colleagues. Talk to them about John Oliver or basketball or Interstellar, or, dare I say, work. But do talk.

Next week, we are back to our regularly scheduled programming.
So please send your questions to [email protected].
I am looking forward to hearing from each and every one of you.


Jobs | February 23