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Managing a compulsive ‘yes’ person

133 replies

Theweedygarden · 03/10/2025 06:18

TLDR: A compulsive ‘yes’ female colleague has made one to many errors and now I need to manage her incredibly emotional, and slightly childish, response.

I line manage someone who manages a compulsive ‘yes’ woman (A). Anything anyone asks of A, she will do. The person I line manage has been off for several weeks now, and although I have always been aware of A’s issues it is now becoming ridiculous and impacting on business need and my time. Her inability to say ‘no’ means she is late actioning things for me and several times this week I have had to step in and tell her she is not to do something. She cannot manage other colleagues, including those more senior than her (which whilst uncomfortable is part of her job and she knew this when she applied for the role), and her desire to consistently say yes to them means we are actually failing to deliver priorities. She seems to rely on more senior people delivering tough messages that, when I was doing her role, I delivered with ease and others doing the same role can also deliver.

Her interactions with colleagues often go something along the lines of;

B: ‘Can you book this room for me?’
A: (more senior) ‘yes, of course. I’ll do it now.’
Me: ‘Absolutely not. It is B’s job to do this.’

C: ‘We can’t do this. X won’t be happy.’
A: ‘Of course I understand.’
Me: ‘Unfortunately, C it is not our problem if X is not happy - our job is to deliver these outcomes, if your contact is not happy with that it is your job to manage the fallout.’

D: ‘We can’t say this. It will upset them.’
A: ‘Of course. What would you suggest?’
Me: ‘The steer from above has been we are to say this, it does not matter if it upsets them. We gave advice on this, our advice was taken under consideration but the steer from above is that we must proceed. You will need to deliver this message directly to V.’

She seems to worry more about upsetting her contacts across the office than she does about doing a good job. It feels almost as though in her mind if they are upset, she can’t be doing a good job. But in reality it’s the opposite - her contacts across the office should be upset because it is their job to push for unreasonable things to keep their external contacts happy, and it is our job to manage them and prioritise ruthlessly.

Anyway, earlier this week I ended up giving her a first written warning and stated that if she did not improve that I would have to put her on a performance management plan. She’s clearly devastated. She’s been crying at work all week, bursting into tears on video calls etc. But she’s also barely spoken to me (leaving messages read but unanswered on our internal system), and yesterday she failed to action something on time and to a decent standard (I received it after COP and it was very poorly drafted, and I had to send it on to my seniors for 09;00 this morning).

I’ve put an hour in our diaries today and told her I want to talk. I need to address the crying, the poor work yesterday and ignoring me when I asked for things to be done.

I know what to say, but I’m a bit torn on how best to say it. I don’t think being gentle will be help, in part because I am not sure I can as she has made some significant errors in judgement recently that have impacted the business and also because she’s an adult and I don’t think I should coddle her because she’s upset. But I know that if I am too harsh she will probably just cry again and that won’t be conducive to delivering the messages she needs to hears. There’s a happy middle, I’m sure, I’m just not sure what it is.

Has anyone ever had a similar conversation with a colleague? And, if so, how did you handle it?

OP posts:
whimsicallyprickly · 03/10/2025 17:48

A is senior and has roughly 200 people in her direct (once or twice removed) management chain depending on her to make effective decisions and lead them. This is not simply her being ‘less effective’ but doing actual, real world, damage to our organisation’s ability to function and harming other colleagues by generating unnecessary work

How the fuck did she get this job? Its obvious that she can't do it and needs to be put on a PIP with clear guidelines which she will fail. Then get rid

Lord 🙄😬😳

whimsicallyprickly · 03/10/2025 17:53

NowYouSee · 03/10/2025 17:32

Under a year’s service? Well that changes it significantly.

if you don’t think a PIP can resort in a successful outcome the only reason to do it is to prove a fair dismissal. But given she can’t bring an unfair dismissal claim at this point, absent discrimination, why go through the pain for everyone? I would speak to senior HR people about looking to exit now. And she should have no claims to settle.

Actually.....this ^

SanctusInDistress · 03/10/2025 18:05

Ignore the others, OP, I get it. Shes there to do HER job, not to people please.

Elzibub · 03/10/2025 18:10

Going to sound harsh but unfortunately in this day and age you can’t just sack someone for being crap at their job !!

Theweedygarden · 03/10/2025 18:17

@NowYouSee we have actually touched on that with HR, but as you say we want to ensure we can categorically prove fair dismissal. We don’t think there is a claim, but better to be safe than sorry and there’s always a risk people go to the press.

The shorter exit, which could lead to a claim, would save us weeks. In the meantime, I can monitor her performance and protect that department and the team as best I can by leaning in more - which is what I will tell her next week (that I will lean in more).

I have never had to manage poor performance before, as I have always been very lucky with staff I directly manage and with this organisation. This is the first instance of poor performance in thirty years, so I do really appreciate the advice everyone is offering.

OP posts:
MrsMickey · 03/10/2025 18:18

Ivw worked with someone like this. Really lovely person, but wants to constantly go the extra mile to help on things that don’t matter. It’s termed a people pleaser. It can come across as bullying when you try to do something about it as they’re the lovely person that helps, and as they are a people pleaser, upsetting you is their worst fear. I’d look up some of the work done by Amy gallo on this as she’s got lots of tactics to handle it (it’s in her getting along how to work with anyone)

GiveDogBone · 03/10/2025 18:24

Sounds like she’s in the wrong role, you describe her one as one which needs her to say no, whereas she gets her rewards from saying yes. I’m a bit stunned you went to a written warning, the result was entirely predictable - it’s destroyed her confidence. I would have expected you to work with her and help her see that it’s in her interest to say no, or to find a role more suited to her. Maybe this happened and you didn’t set it out for space reasons, of course.

But the stick you are trying never works in my experience.

Chinsupmeloves · 03/10/2025 18:39

It sounds like she is just very kind and nice so maybe not cut out for the unpleasantness that clearly has to come with her role and the company. Please show some understanding and empathy to her, a vital.part of being a good boss.

NowYouSee · 03/10/2025 18:42

Theweedygarden · 03/10/2025 18:17

@NowYouSee we have actually touched on that with HR, but as you say we want to ensure we can categorically prove fair dismissal. We don’t think there is a claim, but better to be safe than sorry and there’s always a risk people go to the press.

The shorter exit, which could lead to a claim, would save us weeks. In the meantime, I can monitor her performance and protect that department and the team as best I can by leaning in more - which is what I will tell her next week (that I will lean in more).

I have never had to manage poor performance before, as I have always been very lucky with staff I directly manage and with this organisation. This is the first instance of poor performance in thirty years, so I do really appreciate the advice everyone is offering.

I’m not sure you have the risk balance right here. If it is a 3 month PIP you’re looking at min 3 months, meanwhile discontent will continue to grow within a very large team and stakeholders, you will spend a lot of time managing it and you will have a horrible atmosphere. Everyone will be miserable.

Unless she has protected characteristics and there is any discrimination angle then you really don’t have a risk to manage. And why are you worried about press - she isn’t going to do that and so what if she does - she was an underperformer that got the sack, you’d still have that risk if you took out on a PIP. If she had over 2 years service that would be different.

If you’re worried about press/any real risk of claims then you have protected conversation via HR and offer her the pay for the period a PIP would take plus obviously her notice period. I’ve done this recently with an under performing manager but they did have over 2 years.

I appreciate this rounds cold but ripping the plaster is really likely the best outcome.

Chinsupmeloves · 03/10/2025 18:43

Sorry, my first reaction was that she was new and learning, so yes should know how to handle the role more effectively.

However, again, if it's nature to please and she was the star candidate, maybe these qualities do really work and just need time.

Anon39 · 03/10/2025 18:45

Why aren’t you focusing on managing the people in the office who are asking her to do things outside of her remit.

instead of focusing on the weakest link focus on the communications with senior people who don’t understand the structure therefore you would be preventing her having to say yes

I couldn’t think of anything worse as a junior having to say no to someone senior especially if I felt like I was being scrutinised, it’s your role to manage other people not hers.

ExitViaGiftShop · 03/10/2025 19:00

OP, this person is managed by someone you manage, is that correct?

Do you think you are projecting your inadequacies as a manager onto this poor person? Possibly trying to scapegoat her? You strike me as someone who lacks self awareness. You might find yourself and your way of managing, under scrutiny if this person decides to raise a grievance. If a person is crying at work because of you, then that is awful.

RockyRogue1001 · 03/10/2025 19:26

Eeek!

I don't have any advice because this is not my world, but just wanted to say @Theweedygarden that I TOTALLY get you and the situation, and can see how everyone has bent over backwards to support A.

Capability seems to be your only way forward now.

They're the wrong fit for the job, it seems

RubieChewsDay · 03/10/2025 19:34

Anon39 · 03/10/2025 18:45

Why aren’t you focusing on managing the people in the office who are asking her to do things outside of her remit.

instead of focusing on the weakest link focus on the communications with senior people who don’t understand the structure therefore you would be preventing her having to say yes

I couldn’t think of anything worse as a junior having to say no to someone senior especially if I felt like I was being scrutinised, it’s your role to manage other people not hers.

Because the person in the role should be able to say no herself. She's in a senior position and needs to be able to set boundaries, and one that she needs to be able to do effectively as per the job description for the role.

RandomMess · 03/10/2025 20:20

As someone who has a “Yes” manager who is unable to manage demands I can confirm it’s absolutely miserable and impossible to work effectively under.

Speckly · 03/10/2025 22:33

What appropriate CPD have you offered this person since you’ve been telling her what she’s not good at? Have you offered her alternative strategies and/or genuine support? Does she have any SMART targets to work towards? Have you thought about changing her role? Does she have a positive mentor to go to when she’s unsure what to do or needs to talk?

Unfortunately it sounds like you’ve all just been telling her what she’s not good at and what she needs to do better, without actually putting anything in place to support her to change her behaviours or to help her mental health when it’s obviously taken a real knock. Her saying “it’s just the way I am” screams that she doesn’t know how to act any differently but you don’t seem to have addressed this in any way, just ridiculed her on here for it 🙄

Reading your OP and responses, I think perhaps you should take a long hard look at yourself and question if this is the person you really want to be… you are so derogatory about her emotions particularly. Try a little support and kindness. Honestly, it can work wonders and you’ll really bring out the best in people.

NaanPeshwari · 03/10/2025 22:35

Theweedygarden · 03/10/2025 18:17

@NowYouSee we have actually touched on that with HR, but as you say we want to ensure we can categorically prove fair dismissal. We don’t think there is a claim, but better to be safe than sorry and there’s always a risk people go to the press.

The shorter exit, which could lead to a claim, would save us weeks. In the meantime, I can monitor her performance and protect that department and the team as best I can by leaning in more - which is what I will tell her next week (that I will lean in more).

I have never had to manage poor performance before, as I have always been very lucky with staff I directly manage and with this organisation. This is the first instance of poor performance in thirty years, so I do really appreciate the advice everyone is offering.

Kindly, what you are doing here is saying one thing and doing another thing:

The shorter exit, which could lead to a claim, would save us weeks. In the meantime, I can monitor her performance and protect that department and the team as best I can by leaning in more - which is what I will tell her next week (that I will lean in more).

I'll tell her I'll lean in and be more supportive.

I'll lean in to monitor her more.

It sounds psychologically horrific.

Maybe just be concise with her and try and be a bit less wordy. Outline what you want to see in a few words.

Miaminmoo · 04/10/2025 03:04

If COP stands for ‘Close of Play’ then I can’t bring myself to respond to you.

Doeschangingwork · 04/10/2025 07:44

Being a DD is a big responsibility and she’s paid loads to reflect this. The fact is, the org (maybe you were directly involved) have hired the wrong person - you acknowledge that. It does happen - no process is perfect.
Abd actually, with your tough style, youre the person that your org would want to deliver these tough messages. Youre basically getting her out and she knows this. That’s a major reason why she’s so emotional - she knows she’s going to lose her high paying role. Out of interest, was this a promotion for her? The level below might be her limit? Have you had that conversation with her?
Having an incompetent DD is not great and clearly others can see this - the fact that she being told ‘book it yiurself’ and she accepts means that they are taking advantage of her ‘flaws’. I use that word carefully as in another type of role, it might work to have a senior manager who is so approachable and considerate to junior staff. It shows consideration and actually booking your own flights for example, could be seen as a way of mucking in, acknowledging the other person is busy and has pressures too and youre all in it together type of thing. Therefore, I would also look at why this is happening. You have strict boundaries as to who does what in their roles, but is this actually working? Are you an agile workforce? In reality, perhaps not, but she sees herself as being agile which doesn’t fit?
However, I too would say do not do this one by yourself, you need a witness. I would roll you out for the final death knell conversation but perhaps this isn’t the one. Really work out what you want to say in stages and take someone with you. Then document it all abd get her to agree your record if you can. If she doesn’t agree, youre more transparent about the writing on the wall. Therefore, in answer to your original question, judge whether your style can work for this quite nuanced conversation you need to have, if not, temper it more than you want, and definitely take someone with you. Good luck. Sounds like a nightmare all round.

Theweedygarden · 04/10/2025 09:33

@Speckly the organisation have spent tens of thousands on her professional development, including training and courses despite the fact that no training should be required for someone at this level. Her role is to make decisions and prioritise and opine on big issues, she’s not doing anything technical or specialist. The specialist/technical stuff is done by junior members of staff who put the information to her and she is meant to decide which options will be best for the organisation, taking into account the information she is provided with. She has smart objectives. She refused mentor and refused employee assistance (she called the suggestion she may wish to use it ‘offensive’).

As a business, we have given her far more time (ten months), training and support than being frank we needed to. We could have sacked her months ago but we have tried to support her.

Unfortunately for her, her time is up. Adults who cry routinely at work, after failing to accept multiple offers of help, who accept their issues are negatively impacting not just the organisation but other staff and yet refuse to work on it ‘it’s just me’ and who ignore their management when they are finally put on a formal performance process after months of being warned this was coming, do not get another chance.

My job is to protect the 200 people under her who are suffering as a result of her incompetence, and the business. Her needs - particularly after so many chances and support - do not trump theirs.

OP posts:
Treesandsheepeverywhere · 04/10/2025 09:40

You sound like you've tried everything else OP, as others have said, take someone else in and it's not your job to mollycoddle.

Not sure how to say it in a way she doesn't find offensive but good luck.

LandSharksAnonymous · 04/10/2025 09:45

100% agree with PP.

I can't believe so many posters are failing to understand that the needs and wants of one member of staff do not trump everyone else or the company.

OP asked how to handle the issue/conversation, not whether she was right.

IchiNiSanShiGo · 04/10/2025 10:15

Crying at work and ignoring your boss is completely unprofessional, especially at her level. At this point, however you approach the conversation, she is not going to take it well. All you can do now is keep it factual and don’t give in to the emotional blackmail. Be prepared for her behaviour to get worse, and speak to HR to find out if putting her on gardening leave / settlement might be an option. Her actions are clearly having a detrimental effect, and this might be a better option in terms of protecting the business.

HaveItOffTilICough · 04/10/2025 13:03

I'm surprised how many people think “Awwh, she’s just trying to be nice, she’s obviously struggling, be kind” will wash when it comes to someone clearly not doing their job properly. It’s all very well saying someone shouldn’t be forced to change their personality, but if their personality simply isn’t suited to the job, maybe it’s their job they should change?

Look at it this way. If the OP was here saying the job involved dealing with sensitive situations diplomatically and with compassion, but the person in the role seemed incapable of showing empathy and just said “Tough luck - like it or lump it” when someone was struggling, everyone would be telling her to get this person out. Why is it different in reverse?

ICouldHaveCheckedFirst · 04/10/2025 17:52

She asked for the meeting to be delayed until next week, you say, OP? My money's on her going off sick (been there, albeit with someone much more junior).
Good luck, you really are running out of options.

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