Offsites Where Leaders Can Tell the Unspoken Truth
A quiet, confidential check-in for your leaders while they’re already away from their desks
Most corporate offsites have the same skeleton.
A resort or conference centre. Strategy decks. Breakouts. A consultant with a model. A “wellness moment.” A closing circle where people say the right things about “alignment” and “energy” and then go straight back to overflowing inboxes.
What rarely happens is the one conversation that would make the whole trip worthwhile:
“How are you really doing in this role, in this firm, at this pace – and what needs to change?”
This service exists to make room for that potentially awkward yet highly vital conversation.
The gap your offsite doesn’t touch
You already know the formal agenda will get covered: markets, strategy, regulation, budgets, initiatives. You may even have a coach or facilitator to keep the room moving.
What tends to be missing is a safe place for leaders to say the things they will never say in front of colleagues, reports, or their own coach who is measuring them against KPIs.
Things like:
“I’m tired in a way sleep isn’t fixing.”
“I’m not sure this role fits me anymore, but I don’t know how to say that without sounding disloyal.”
“The targets and the rhetoric don’t match. I can’t say that in the room without being labelled negative.”
“My health and family are taking hits I’ve stopped admitting even to myself.”
Those thoughts do not belong in plenary. They also don’t disappear just because the bar is open and someone ordered greasy sliders.
I’m there for that layer.
What I actually do on your offsite
I attend your away day or retreat as a quiet, external advisor. I am not on stage, not running your agenda, and not there to judge performance.
My role is simple:
To provide confidential one-to-one conversations for your key people, focused on how their work actually feels and what, if anything, needs to shift.
In practice, that usually means:
Short, pre-booked individual sessions spread through the offsite, so people know they have a private hour with someone who understands their world and has no stake in internal politics.
Space to talk about the things that don’t make it into 360s and engagement surveys: suitability of the role, early burnout signals, succession anxiety, moral fatigue, quiet boredom, misalignment between values and incentives.
Gentle but direct questioning about the next decade, not just the next quarter: whether this is still the right work, in the right place, with the right people, at a sustainable pace.
I am there as a confidant, not as another coach trying to wring more “performance” out of people who are already stretched, exhausted, and quietly unravelling.
How this is different from executive coaching and facilitation
You may already have:
Executive coaches working with your senior people
A facilitator running the offsite
HR business partners and people leaders
All of those can be useful. None of them are neutral.
Coaches are often hired to improve performance inside the existing structure. Facilitators are there to serve the agenda. HR has a duty to the organisation as well as to individuals.
My allegiance is narrower and clearer: I am there for the human being in the role.
I understand boards, investment committees, mandates, product grids, regulatory pressure and the realities of managing capital. I also understand hairline fractures: the marriage running on fumes, the creeping insomnia, the resentment of always being “the reliable one,” the quiet sense of having drifted far from the life they meant to build.
I do not write performance reviews. I do not report back on individuals. I do not rank your leaders. I speak plainly with them about their reality and ask them to consider small, concrete changes they can live with when they go back.
What your organization receives (and does not receive)
You do not receive a dossier of gossip or a back-channel assessment of who is “strong” and who is “weak.” I will not help you build a secret scorecard.
If – and only if – we agree in advance, I may summarise broad, anonymised themes for a small sponsoring group after the offsite. Things like:
“Several leaders are carrying unsustainable loads and assuming they must absorb them alone.”
“There is a consistent mismatch between the way risk is spoken about in the boardroom and the way it is felt by people closer to the coalface.”
“Succession anxiety is real; mid-career leaders don’t see a believable next chapter here.”
No names. No identifying detail. Just patterns that help you see what your people already feel.
The real value, though, sits with the individuals:
One senior manager finally admitting that a “dream role” is quietly harmful and beginning to plan a better-fitting path inside or outside the firm.
One partner deciding to cut back on performative busyness and actually delegate.
One executive noticing how much of their anger at work is rooted in exhaustion, not in “difficult staff,” and committing to real rest before the next decisive quarter.
Those are not things you can force in a room with a microphone. They happen in honest, private conversations.
Where this fits in your offsite
There are a few natural ways to weave this in:
As a parallel track. While the main agenda runs, selected leaders have pre-scheduled check-ins with me in a quiet side room. No fanfare, no big announcement.
At the edges. Early morning and late afternoon slots before and after formal sessions, for people who prefer not to step out mid-day.
Before and after. Some organisations choose one conversation before the offsite and one afterwards, using the retreat as a natural break in the year to think more deeply.
We design it together so it supports your offsite rather than competing with it.
Who this is for
This offering makes most sense if:
Your firm works where financial capital and societal consequences intersect.
Your leaders are smart, heavily credentialed, and often introverted.
You suspect that some of your best people are quietly running beyond their human limits and will not say so in a survey or a plenary session.
You are more interested in preserving thoughtful leaders for the long term than squeezing out one more year of unsustainable output.
If you only want someone to rev everyone up and send them back out “more motivated,” there are plenty of consultants who will oblige.
If you want your leaders to have at least one place this year where they can stop performing, name what is actually happening, and take a few small, sane steps toward a more sustainable way of working, that’s where I come in.
If you’re considering this
If you’re planning an offsite and would like to explore adding this layer, the next step is simple:
Connect with me directly with:
The nature of your organization
Where and when the offsite is likely to be
How many people you’re thinking about
From there, we can see whether this is a genuine fit for you and for me. If it is, we design something that respects your culture, honours confidentiality, and gives your leaders what they rarely receive: a chance to tell the truth while there is still time to act on it.