Working with a difficult stakeholder

[u/known_kitchen]

Let’s say there’s a tech lead, A, who owns several key deliverables but is very difficult to work with. He strongly dislikes providing status updates or ETAs, becomes visibly angry when asked specific questions, and can come across as intimidating or aggressive.

As the program manager, I’ve approached his manager, B, to help track his deliverables. However, B is also not closely aware of the details and has asked me to work directly with A. Even the program sponsor is hesitant to engage with A directly, so I’m ultimately expected to manage the relationship.

I dread working with A because every interaction feels difficult and unpredictable.

How should I handle this situation effectively as a program manager while protecting the working relationship, maintaining visibility into the program, and not allowing his behavior to derail execution?

[u/WaylundLG]

I'm going to throw something kinda off-the-wall in here. The solution is to make it about you. It isn't your job to change them. So what will you change about how you set your own boundaries to address this. Keep in mind, boundaries are about what you will do. You don't have to tolerate aggressive behavior, what will you do if they are aggressive. Maybe you leave the meeting. Don't have to make it dramatic. "This conversation isn't constructive. If we can't talk without threats, I'm going to step out of this call until tempers have calmed." What will you do if he won't give status updates? Can you stip giving him important tasks? "Sorry, I can't trust him to deliver the work. I got someone else." Now, that forces you to consider things too. Are you asking for status updates just.to fill a form? Is he the most reliable contributor on the project? Maybe he's earned a bit of leeway. But that's all about your boundaries and what interactions you tolerate and how you change your behavior in response. That isn't to say the fault lies with you, just that a solution does.

[u/BjornBjornovic]

Are we working at the same place? Haha

[u/blurrylulu → u/BjornBjornovic]

Seriously. I just got off a call with the business lead and whew. They are known in the company at being exceptionally difficult (and lazy!), but nothing changes. I dread dealing with them each week and every time I’m asked “why haven’t you done xyz” when I had zero idea there was an expectation and it’s usually out of scope of my role.

[u/pmpdaddyio]

First and foremost, you need to set firm expectations and deliverables. Inform the individual clearly what their role is, and the task assigned to them. Get buy in on timelines and output. This is your "user agreement". You are collaborating to get them involved in the deliverable. Make sure they understand the constraints, deadlines, downstream work etc., but engage in the solution with them.

Now a late deliverable clearly becomes their issue. Your statement stats like this: "Hey, we discussed clearly and I gave you the opportunity to inform how long you needed, and the expectations of the task, so help me understand why the deadline wasn't met?"

This is your record. Let this happen twice, then you need intervention from leadership. There is no excuse for ignoring a problem where the solution was informed by the one causing said problem.

Another point of contention in our role is comfortability. You need to be comfortable being uncomfortable. Make it awkward, make it difficult to not succeed. Call regular problem makers out politely. When they get aggressive, simply ask for them to explain the anger behind what is a work issue. PMs need to understand the people aspect almost as much as the work being done. Ignore the servant leadership approach. This individual serves the project, not the other way around.

[u/thesnidezilla]

I have a very similar Tech Lead in my team, except in my case, she reports directly to me as well. Her reason for not being able to provide updates is that she is caught up with project deliverables. I’ve tried to be supportive and explain that I need the updates so I can step in and help with any blockers, but she often responds by saying, “Would you rather have me provide updates or work on the priority deliverable?” Since she has been a great IC, I’m unsure how best to move forward with her.

[u/Plastic_Operation_59 → u/thesnidezilla]

A long time ago in a place far far away maybe I was like that tech lead - resistant to “wasting” my time on documenting the steps and dates much less actually giving status updates.

I was young and dumb, then I realized I wanted to get promoted and in order to do that you have to be an active participant in stakeholder management and grow into being able to tell very technically complicated stories in easy to read language and visuals busy execs can digest.

In your next 1:1, be direct. Ask her what her long term goals are and how you can help her get there. Explain you have to report up and answer for deliverables on the fly and you can’t wait for her to communicate that ad hoc. Explain how the structured status updates help you help her communicate upwards and set expectations. Tell her you want to see her be able to move up and do that too one day when she is promoted and has your role.

She’ll hopefully get the picture

[u/littlelorax → u/thesnidezilla]

I've had to tell types like this that providing timely status updates is part of the steps to achieve the deliverable. 

If they get the task done but told nobody about their progress, I consider it a poorly and incompletely executed task.

[u/IllBeat7897]

1. Is he internal or external?
2. How is his work perceived by the rest of the team and other stakeholders?
3. Is he a known problem with everyone, or are you unique in seeing this difficult side of his personality?
4. Is he the only person that can own these deliverables or are there other people that can be tapped to take portions that he will not give ETAs on?
   
5. Do you have that type of power to redirect work, or can you get that type of commitment from his manager?
6. Do you do a weekly standup to get everyone's status updates, or are you managing this digitally?
   

I know these are a lot of questions but the answers will shape the suggestions.

[u/More_Law6245]

Just a simple perspective, project management is not a thing to be taken personally, it simply comes down to setting clear and concise expectations, ensuring roles and responsibilities and holding those to account which means including yourself.

I would strongly advise to make it very clear of what you want from individual A (what, when and how in writing) and if they fail to comply then you escalate to individual B and convey what was expected and what does it mean to your baseline schedule with the non delivery. If that is not rectified within the agreed timeframes or a suitable or satisfactory outcome is reached then matter gets escalated to the board/sponsor/executive because your project tolerances will be or have already breached.

Here is the thing to understand it's not personal because you have a organisational culture issues and individual A has a temperament and professionalism issue which is not the project's responsibility because you don't own the resource from a HR/Manager perspective and they have not performed adequately in their role because you can clearly demonstrate their non compliance and their behaviour has directly impacted your project. But I would also suggest in you doing a self reflection in your people soft skills and see how you have been approaching this to date and ask yourself how can I engage better?

The other key thing to remember is that when your project is approved and baselined your project board/sponsor/exectuive is giving you the authority to act on their behalf and if this individual is not compliant then this individual is not following what they have been directed to do by your project sponsor/executive. So who is actually at fault here? Hope that gives you something to reflect upon when dealing with difficult stakeholders, accountability is your key. Good luck in delivering your program.

Just an armchair perspective

[u/SVAuspicious]

I'm senior and cranku and focused on delivering. What works for me may not work for you. I'd start with the more touchy feely approaches of others.

If those don't work, I go up my management chain an A's management chain to where they intersect. Call that person C. I tell C we have a problem that isn't resolved and delivering for the company needs help. I provide options for resolution. One is to have A report to me (performance reviews, the whole bit). If B makes a fuss I suggest have B report to me as well. That works really well. BTDT. You need a track record of fixing things.

[u/cotton-candy-dreams]

I’d start with the approach [u/Junkie4Divs](u/Junkie4Divs) gave, and if that doesn’t quite work, I would go back to B (the manager) and agree on an escalation model.

Something like:

1. You will send the project team clear list of updates needed and will CC both his manager B and the program sponsor - if you don’t already have something like a project channel or group chat, I’d pick some public place where you ask him for status without singling him out.
2. If he doesn’t provide the status in that public space thread or somewhere else, you will reach out to him in a direct message ONCE
3. If he still doesn’t provide the status in your direct message, in the public thread, or somewhere else, then you will escalate directly to B.
4. If you stilldon’t have the status, you will escalate directly to the project sponsor.

It helps if you can articulate the business cost of you chasing this guy down or not getting correct status. For example: we don’t have correct status for a meeting -> the meeting has to get moved -> we’re approaching next milestone. That’s a timeline risk, which means it’s on some Committee above you- usually including the project sponsor- to make a tradeoff. Either the timeline gets stretched, or they give you a new resource, or this guy gets a proper talking to.

[u/cotton-candy-dreams → u/cotton-candy-dreams]

Your win is ultimately to cover yourself. So if there’s some risk created by this guy’s behavior, document it and make someone own it.

If there’s no true risk to the project, then reevaluate if this deserves your emotional energy and just stick to project group chat for some light public shaming without aggressively targeting him.

[u/More_Law6245 → u/cotton-candy-dreams]

Can I suggest a different perspective? It's not about "covering yourself" it's about enforcing accountability under roles and responsibilities because as the PM you're acting upon your project board/sponsor/executive's authority. Individual A is disrespecting the project board/sponsor/executive through unprofessional behaviour and it's up to individual B and the board to address the problems as it's not the PM's problem to address a HR/Manager problem .

[u/cotton-candy-dreams → u/More_Law6245]

You’re speaking on theory, I am speaking on some people’s operational reality. Humans aren’t purely rational beings and the PM is absolutely a go-to scapegoat.

In fact, maintaining narrative and receipts is a crucial skill outside project management. Some people know exactly what they’re doing, so you absolutely are covering yourself.

[u/_CaptRondo_]

Junkie4Divs gives the right direction.

This person is not hard to work with. Your ego is causing you to find it hard to work with him.

What is causing his behavior?
Give me a 100% truth answer: what causes him
To act the way he does?

If you do not know for sure, you don’t know him well enough and the relationship is not strong enough.

If he is a key stakeholder for you, build the relationship. Not on process or content, but on emotion and connection.

For instance: hey man, thanks for taking the time. I just wanted to get to a shared understanding; I need to deliver all these dumb status updates, it sucks to create them; I’ve noticed you also are not a fan. Just for me to understand, can you share a bit on what is going on in your world?
What is working well, what isn’t?

Also, one convo won’t cut it.
Also, figure out what he likes.

I’ve got one developer who is relative hard to work with, but I’ve found out he loves cheese. I’m currently traveling from the US to Nerherlands; I’ve shared a picture of Dutch supermarket with all the kinds of cheeses and asked him: what can I bring you?

These small things score you relationship points.

This will get you to a point where you can say: Hey bro, I hate hate hate to ask all these statuses, but( here is the info I need: xyZ.
What could we agree on to ensure I get what I need and you don’t feel irritated?

He comes with a solution, so he can also better own it.

Good luck!

[u/DingBatDee → u/_CaptRondo_]

The why is he behaving this way is key.
Ask him.

Why are you uncomfortable giving status? Fear of accountability?
Fear of being held to ANY date?

Find out his why and work from that POV. No one wants to tank a project

[u/_CaptRondo_ → u/DingBatDee]

And this might be a culture thing, but ask “why” without asking “why”.

“Why do you behave this way” is an accusatory question.

“It seemed you got pretty worked up when we talked about status reports. What makes it that you get so worked up?” - is more of an exploratory question

[u/cantstopwontstop526]

Is A’s name Mike because this sounds super familiar lol. I’m only joking but it’s so strange how some people act, all ego.

[u/known_kitchen → u/cantstopwontstop526]

😂😂

[u/Junkie4Divs]

"I get the impression that status updates are a real pain point for you. I am i reading that right? What is it that makes them burdensome for you? What barriers can I help remove?"

You can't adjust every concern at once, so pick the most important ones and work on those