Stuck with no direction but no autonomy

[stuckinthemiddl]

Hi, I'd love some perspectives on managing a situation with my boss.
I'm in a strategic/direction setting role within a team and my boss is also responsible for the people delivering on this strategy.
The challenge I have is that my boss is not prescriptive or clear when setting the brief - wants to be iterative and lean into ambiguity but then is very clear about the outputs she wants when the answer she gets isn't what was in her mind.
It's very frustrating because I'm happy to use my initiative and decide an approach etc (and am at a level where I'm paid and experienced to) but what's happening is rather than being judged on the outputs/results, it's wrong if I haven't successfully second guessed what my boss has in mind. I could handle this if they could be prescriptive from the outset but they're not so I'm stuck with no direction but also no autonomy.
Any advice gratefully received! I enjoy what I do but this is starting to knock my confidence and demotivate me because I can't get anything right unless I'm a mind reader...
Thank you!

The challenge I have is that my boss is not prescriptive or clear when setting the brief - wants to be iterative and lean into ambiguity

Can you agree on an ultimate objective or the problem you're trying to solve for your customers or the business?

but then is very clear about the outputs she wants when the answer she gets isn't what was in her mind

Do you mean she's prescriptive about the format of the outputs or the content?

So you have a control freak boss.
So you need to organise your work to (aggressively) micromanage the dataflow to your boss.
If you know the output needed, you need at least 2 paths to get there.
Once you have 2 paths you need to have a meeting and get sign off / buyin for one or rejection for both.
Only by forcing a clear brief by excluding options will you be able to create a clear path.
Stop charging off to solve the problem on your own, your boss needs to feel the solution was her idea to begin with.🤷
Once that happens you need to convince the boss that you both think the same and come up with the same ideas anyway.
She buys into that idea and learns to trust you.

In real life if you can't manage the boss's expectation the best long term solution (for work life balance), is to organise a new boss/job.

Thanks for the reply.
We can agree on the problem to solve, usually...
It's the next stage - more content than format because there are so many ways of solving a problem and although it will be insight/data driven, she will always find a different way or looking at it or a slight change to the brief.
I think the most frustrating bit is that neither of us are wrong, it's just subjective and has to be judged on outputs. I also get the pressure and feedback from the wider team that they just want to get an answer quickly and they don't see the value in going round in circles and debating because it reduces the time to deliver and ultimately it's an intellectual debate and doesn't change things much. She is broadly aware of this feedback but doesn't agree or take it on board, her solution would be to do it herself to get to a 'signed off' answer which obviously makes me feel shit! And she doesn't have time to do this, she has a big team to manage and remit to manage up too.
Sorry, venting now!

It sounds as though you need to baseline the problem to be solved and then propose the approach to be taken to explore it, and some milestones or checkpoints to review and iterate on the solutions. If she's not in agreement with the timeline for iteration then you'll need to discuss and adjust, or make your case differently. But it sounds as though you need to agree upfront some principles about ways of working and timelines.

Are you working in sprints?

Hahaha, I was being diplomatic but you've got it in one!
I think you're totally right about getting the brief signed off and managing her so that it's her idea and she's bought in. I need to try and do this more, the challenge is she's so busy (can't delegate...) that getting her time is also challenging so I don't want to lose time waiting for her. Side note, she has ADHD and also struggles with replying to emails and likes to talk stuff through and open up new avenues of thought.
I do think this is the last chance now to see if I can make it work, a lot of people have left the business for similar reasons and I'm stubbornly determined to make it work because I've had the some success in aligning to her thinking and getting somewhere but I'm struggling now!
Thanks for the advice

Sounds as though there's also some expectation management to do with the wider team about what is going to be clear and when .

Are you and your boss agreed on the level of certainty or confidence needed in a particular approach/solution before you proceed?

Thank you, yes you're exactly right that the upfront agreement and permission to play within guardrails would help. I will try and have this more structured approach, she just struggles with anything linear and agreed - she'll happily change the brief/approach regardless of it already being agreed and present that as a positive 'good to iterate', 'be comfortable with ambiguity'.
It's really helpful to write this because it's just quite an impossible situation. I think I need a serious conversation about ways of working and contracting.
Thanks for your reply

In theory we've done this and agreed but the reality doesn't match up and because she's the most senior person actively involved (reports to exec, not involved day-to-day) she calls the shots and gets to break her own rules!

Time can be an informal 2min chat each morning and afternoon while you are standing in the doorway drinking your coffee.
You get the agreement and enter the change into the brief and add a single FYI update to the email chain of dear boss made agreed change come back to me if anything else is needed. She may not read the email but cant "blame" you for not doing what she agreed as she agreed by not offer an alternative.

But if the job know her managemet style is a loosing staff, they chose to keeper either because the business is badly managed or they like that style of management.
Don't stay to "win" because that is not likely to ever happen.

I would maybe draw up something showing the process and play it back to her, emphasising the periods of exploration of ambiguity and the review points where findings will be reviewed, label the iterations. Basically demonstrate to her that you are embracing a process that leans into ambiguity and then iterates to burn down on it so she thinks '@stuckinthemiddl gets it, I understand and am happy with the timelines, and know where and when I input/steer'

(If, having given this a try you find she's still micromanaging then you need to feedback to her that you think you'd work better if you could agree alignment and autonomy)

Really helpful, thanks a lot @AnSolas @Whataretheodds
I'll have a think how I can give her a view of the process with lots of opportunity to input and see how that goes.
WFH makes the more informal check ins tricky unfortunately but we'll find a way...
And yes, you're right I won't 'win', the struggle is I love my job and she's great to work with in some ways - I'm all up for a bit theoretical debate about different ways in but when the rubber hits the road and we need to deliver, it's HARD.
Thanks again!

Good luck let us know how you get on