How to deal with a senior leader who is frequently finding shortcomings with others' work?

Question

I am dealing with a senior leader (let us call him John) who always seem to be pointing out others' mistakes and shortcomings in everyone's work via email.

John frequently does this to architects, managers, etc. and although others don't like it they tolerate it because there is no specific person that one could escalate this issue to without creating a big fuss about it. John is a senior architect who reports directly to CTO, so any escalation regarding him has to be escalated to the CTO which would create a lot of drama. Everyone thinks it is not worth it and they just tolerate his behavior.

John is not consistent with his behavior. He is generally okay in face-to-face conversations. It is only in emails where he sometimes appears to be mildly caustic. Sometimes the issue he points out in email are genuine issues but many times they are not genuine. Here are some examples of issues that are not genuine with my commentary in parentheses:

• "You guys should have done the redesign work by the last sprint." (Actually, it was agreed upon that the redesign work has to be done at some point but it was never communicated precisely exactly when that work was supposed to be started or finished. Further, John is not our boss. We have a different boss who is the one who decides what we work on in which sprint).

• "You guys did not attend meeting about the hardware purchase." (Actually, our guys were never invited to that meeting.)

• "The document you wrote is missing details about future growth plan." (Never mind the fact that the person who wrote the document wrote it voluntarily to share what he knows about the current project with his team. John was not even the primary audience for the document. He was in the recipient list out of courtesy (FYI basis). Most of us are thankful that this guy wrote this document on his own although nobody asked him to do so. But John does not have a word of appreciation for this volunteer work. He has an issue that the document missed a good-to-have but not-so-critical detail.)

Some of these are mildly important things and some are trivial. Most of us do not choose to retaliate because it would look petty. It seems frivolous to be responding with something like, "But nobody invited us to that meeting!"

Have you faced such a senior leader? What is the right way to deal with it?

Answer 1

Document everything, then reply to his emails with the documentation.

You guys should have done the redesign work by the last sprint.

I think we agreed that there'd be a delay in our meeting on the 12th? ah, I have a follow up email here.

You guys did not attend meeting about the hardware purchase.

Sorry John, we didn't get the meeting invite. Are you sure you sent it to us?

The document you wrote is missing details about future growth plan

That wasn't an official document, John. If you want to follow up with Dave, he might be able to help you.

Since John is an otherwise nice guy, according to your question, nothing harsher than gentle reminders and replies to his emails should happen. If you can find a way to let him save face as well, all the better.

If you have a really good relationship with John, you may want to approach him privately and ask him to verify with you, or someone else on the team before broadcasting emails. Tell him that you don't want to contradict him publicly, and things are better if they're kept within the team.

That might put an end to his email rants.

Answer 2

Either John genuinely cares about all these aspects and wants to see them improved, or he's a nitpicker that just takes delight in picking holes in other people's work rather than expending any effort himself.

Most of us do not choose to retaliate because it would look petty. It seems frivolous to be responding with something like, "But nobody invited us to that meeting!"

You don't retaliate by responding with excuses, you simply assume good intent (that he genuinely wants to be involved in making sure your work is up there with the best) and make sure you ask for his input and keep him updated at all stages.

So using your examples above:

You guys should have done the redesign work by the last sprint.

You simply make sure he has the full, thorough version of events:

Hi John, the redesign work for x wasn't scheduled for the last sprint as we had a b and c to complete which were deemed a priority. This has pushed the redesign back somewhat. Have you had pushback from clients or anyone else that's escalated the redesign, and if so could you keep us in the loop? Tim (cc'd) is responsible for assigning priorities for sprints - Tim, could you fill John in on any update on the planned status of the redesign work, and if you've a rough idea of if it'll make it into the next sprint? Thanks!

For the next one:

You guys did not attend meeting about the hardware purchase.

Then you write something similar, saying that you weren't invited and ask him if he could:

• Share the findings of that meeting, and forward you on the minutes;
• Ensure that he chases the person who set up that meeting to make sure that you're on the invite list.

For the third point, the original author can reply and say that he's not familiar with the growth plan, but he's given John edit access and it'd be appreciated if he could fill in that missing piece.

If John cares and puts in effort, then great - he pulls his weight, contributes, makes sure you guys are in the loop and everybody wins.

If John doesn't care and just likes picking holes in everyone's work, then he'll likely stop writing those emails when they cause him, rather than other people, to have to expend effort.

Answer 3

What is the right way to deal with it?

Pick your battles.

When you get something like:
"You guys did not attend meeting about the hardware purchase."

Respond to something like this because he is basically calling-you-out as irresponsible.

A short response to him indicating none of your team was invited (check with them first!) is appropriate. Might be worth CC to the CTO, but that would depend on his/her personality.

He was in the recipient list out of courtesy (FYI basis).

Stop doing that unless the CTO has specifically said that you should.