10 May Why People-Pleasing Directors Struggle to Sell Themselves And What Has to Happen First
Executive Leadership Coaching, Blog
On LinkedIn strategy, recruiter relationships, and the step that comes before both.
People-pleasing directors struggle to sell themselves not because they lack capability or strategy, but because something has to happen first. The Directors I work with often tell me they need to work on their LinkedIn presence. Or get better at talking to recruiters. Or finally learn how to sell themselves properly. And they are probably right. Those things matter enormously.
I was reminded of just how much recently, walking through the Swiss valleys, listening to a conversation between Xhoni Mimillari, a LinkedIn strategist whose work on personal brand and visibility I have followed with genuine respect, and Edvin Vosylius, who specialises in sales recruitment and understands better than most what actually moves the needle in those conversations. The conversation was good enough that I kept walking long past where I had planned to stop.
But somewhere on that path something crystallised. Something that feels almost counterintuitive to say out loud. For a certain kind of Director, those steps, as valuable as they are, can feel just out of reach. Not because they are too complex. But because something needs to happen first.
They have not yet developed a clear enough relationship with their own value to communicate it without apology.
Why People-Pleasing Directors Struggle to Sell Themselves
The Directors I work with who feel most stuck are almost never stuck because they lack capability. Their track record is extraordinary. Their potential is visible to almost everyone around them except themselves.
For a people-pleasing Director, self-promotion does not feel like strategy. It feels like arrogance. Like taking up too much space. Like the kind of behaviour that makes people think less of you rather than more. So they wait. They deliver. They assume the work will eventually speak for itself.
And then they watch someone else, someone with less experience and considerably more ease in their own skin, get the conversation, the introduction, the opportunity.
The block is almost never about not knowing what to do. It is about not yet having a clear enough relationship with their own value to communicate it without immediately wanting to take it back. Which is why the order of steps matters enormously. If you recognise this pattern, find out more about my executive leadership coaching programme.
Step One: Clarity on Your Value
Not what your CV says. What you actually believe about what you bring, without the apology attached to it. This is inner work. It is also the foundation everything else is built on.
For people-pleasing Directors this step is almost always the bottleneck. Not because they lack self-awareness — most of them have considerable self-awareness. But there is a significant difference between understanding your value intellectually and having settled it somewhere more real. Settled it deeply enough that you can communicate it in a high-stakes conversation without the apology creeping back in. Research on executive self-awareness and leadership effectiveness consistently confirms this gap is real and costly.
Step Two: Learning to Articulate That Value
In a sales conversation, in a recruiter meeting, in the room where it matters — with precision and without the over-explaining, the softening, the slightly desperate quality that creeps in when a person has not yet fully settled the question of their own worth.
Authentic examples. Real figures where relevant. Said once, clearly, and left there. No pushing. No begging. No performing confidence you have not yet found. The people-pleasing Director who has done step one properly does not need to over-explain. They say what is true, with the steadiness of someone who has already resolved the question internally, and let the other person respond.
Step Three: Visibility, Relationships, and Conversion
This is everything Xhoni and Edvin mapped out so well, and between them they cover both sides completely. The sales conversations that convert not because of pressure or persuasion but because the value was clear from the start. The LinkedIn presence that makes the right people find you before you need them to. The recruiter relationships built with genuine curiosity long before urgency arrives.
What struck me most about their conversation was not any single tactic. It was the integrity running through all of it. The idea that the best visibility, the best recruiter relationships, the best sales conversations are all built on the same foundation: knowing what you bring and being willing to say it clearly.
Which is exactly why step one cannot be skipped. Without it, the articulation tends to become over-explanation. The LinkedIn content starts to feel curated rather than true. The recruiter conversation gives away just a little more than you meant it to. Get step one right and everything in step three becomes considerably more available. And considerably more like you.
A Note on Sequence
This is not a criticism of LinkedIn strategy or sales methodology. Both are genuinely valuable and the work Xhoni and Edvin do with their respective clients produces real results.
It is an observation about sequence. And about the specific way people-pleasing patterns interfere with the practical steps that everyone agrees matter. The inner work is not instead of the visibility work. It is what makes the visibility work actually work.
If you are a people-pleasing Director who recognises this bottleneck, the pattern-mapping call is a good place to start. Thirty minutes. No pitch. Just clarity on whether this is the right work for you at the right time.
Becoming the leader your next level is already waiting for.
Danguole Litvinskaite, The Leadership Coach Exceptional & Exhausted Senior Leaders Eventually Find
Frequently Asked Questions
Why do capable Directors struggle to sell themselves even when their track record is strong?
Because for a people-pleasing Director, self-promotion does not feel like strategy. It feels like arrogance. Like taking up too much space. Like the kind of behaviour that makes people think less of you rather than more. So they wait, they deliver, they assume the work will eventually speak for itself. The block is almost never about not knowing what to do. It is about not yet having a clear enough relationship with their own value to communicate it without immediately wanting to take it back.
What needs to happen before LinkedIn strategy and recruiter relationships can actually work?
Clarity on your own value. Not what the CV says. What you actually believe about what you bring, without the apology attached to it. Without that foundation, the LinkedIn content starts to feel curated rather than true. The recruiter conversation gives away just a little more than you meant it to. The articulation becomes over-explanation. Get that step right and everything else becomes considerably more available. And considerably more like you.
What is the difference between understanding your value and having truly settled it?
Most people-pleasing Directors have considerable self-awareness. They can describe their value intellectually with precision. But there is a significant difference between understanding it and having settled it somewhere more real. Settled it deeply enough that in a high-stakes conversation, with genuine pressure in the room, they can say what is true with the steadiness of someone who has already resolved the question internally. That gap is where the real work lives.
Is the inner work instead of the practical visibility and sales work?
No. LinkedIn strategy, recruiter relationships, and sales conversations all matter enormously and produce real results. This is an observation about sequence. The inner work is not instead of the visibility work. It is what makes the visibility work actually work. For a people-pleasing Director who skips that step, even the best external strategy tends to leak. The question is not whether to do the practical work. It is whether the foundation is in place to let it land.
About the Author
Danguole Litvinskaite is an executive leadership coach based in Switzerland, specialising in helping exceptional and exhausted senior leaders advance without losing themselves in the process. With 14 years in investment banking across 4 countries, an ICF PCC credential, and 3,000+ executive coaching sessions, she works with senior leaders in tech, finance, consulting, and global financial institutions. Her 3-month intensive, The Integration Method, addresses the overdelivering pattern at the level where it actually lives, combining corporate strategy, leadership psychology, nervous system regulation, and career navigation. Clients include senior leaders at the largest tech companies, Big 4 firms, and global financial institutions.
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