Offsites and strategic planning sessions, run by an operator.
Not a neutral moderator with a flip chart. I have sat in the seat these rooms report to, and I know which conversation the room is avoiding.
The offsite is the most expensive meeting your company runs: ten leaders, two days, a quarter’s momentum riding on the room. Run well, it compresses six months of drift into two days of decisions. Run badly, it is a slide deck nobody opens again.
Executive offsites, planning sessions, working sessions, retreats.
Different rooms, same discipline: agree the outcome before anyone books a flight, say the true thing while everyone is in the room, and leave with decisions that have owners and dates.
Executive offsites
Two days out of the building for the leadership team, when alignment needs a reset: after a pivot, a reorganisation, a new leader, or a year that did not go to plan. You leave with a plan the whole room owns and decisions that have owners and dates.
Strategic planning sessions
Annual or quarterly planning, done properly: the strategy translated into priorities people can actually run. You leave with the year turned into an operating rhythm, not a binder that gets opened once.
Leadership team working sessions
A half day on the one problem that will not die in email: decision rights that were never settled, an initiative that stalled, two functions quietly pulling apart. Small scope, real decision, same structure.
Executive retreats
The longer arc, where the team itself is the agenda: trust, candour, and how the room handles disagreement. The business problems come along for the ride, but the team is what leaves different.
Why an operator in the room changes the outcome.
Most facilitators are neutral by design: they keep time, keep the peace, and keep to the agenda. That neutrality has a cost. When the room politely agrees to a plan that cannot work, a moderator writes it on the flip chart. An operator says the quiet part out loud: this plan assumes two things your own numbers say are not true.
I have sat in the seat these rooms report to: founder and CEO through a Nasdaq IPO, senior executive at New Relic and Cox Automotive, PE-backed operator in startups, unicorns and turnarounds. I know what alignment costs when it is fake, what an operating rhythm looks like when it actually holds, and how decision rights get settled, including in the mess after a merger. Naming the conversation the room is avoiding is the job.
My own teams knew me as a player and a coach, and that is how I run a room. I will hold the process, and when you want it I will weigh in with operator judgment, clearly labelled as opinion. You choose the mix.
Before, in the room, after.
The work before the work
One-on-one conversations with every seat in the room before anyone books a flight. Where useful, a short assessment pass on personality, EQ and how the team handles conflict. We agree the outcome in writing: what must be decided by the time the room empties.
Operator-led, not moderated
A structure that makes it safe to say the true thing, and a facilitator willing to name what the room is avoiding. Working agreements up front, disagreement surfaced early, and decisions that leave with owners and dates.
The 30-day follow-through
The offsite has to survive contact with the next quarter, so we follow through on the operating rhythm for thirty days. The point is not a great two days. It is what the company does differently in the ninety after.
The operator’s side, and the human one.
I bring both sides of the room: the operator’s side, as a public-company CEO, senior executive, and PE operator across startups, unicorns, and turnarounds; and the human side, trained, with a BS in Psychology, graduate work in counseling in progress, and ICF and CEC certifications. Where useful, sessions are assessment-informed: personality, EQ, and 360 feedback instruments chosen for the team.
That matters because the hardest part of any offsite is not the strategy. It is getting ten smart people to say what they actually think while the boss is in the room. That is a psychology problem, and it responds to structure. The standing version of this work, leader by leader, is my executive coaching.
The first offsite.
Names and companies withheld. The situation is real.
The new leader’s first offsite
Alignment · new leaderA new leader inherited a team he did not build and a room full of people deciding what to make of him. We used his first offsite to skip the six months of circling: what the team actually believed about the business, what they needed from him, and what he was asking of them, said out loud with a structure that made it safe to say. He left with a team that had chosen him back.
From rooms I have run and teams I have led.
Ken led our $160M+ cloud, engineering, and DevOps modernization across a $3B+ portfolio. He brought clarity, velocity, and accountability to every initiative.
As COO, Ken led with clarity and focus, revamping our GTM motion, cutting burn significantly, and driving cross-functional alignment across Product, Sales, and Operations.
He brought a rare mix of focused execution, operational rigor, and infectious positivity. He drove alignment and morale even as we reduced burn by 50%. His leadership during our acquisition was steady, thoughtful, and deeply collaborative.
Based in Alpharetta, Georgia. I work remotely with leaders everywhere, and on-site when the work calls for it: offsites, working sessions, and engagements anywhere in the country. Atlanta metro in person is easy. (629) 304-8755 · ken@kengavranovic.com
The ones people actually ask.
What does a strategy facilitator do?
Designs and runs the session so the leadership team does its best thinking: the right questions in the right order, a structure that surfaces disagreement early, and a room where the true thing can be said. The facilitator owns the process so the team can own the decisions. I add one more thing: operator judgment about whether the plan the room is converging on can actually work.
How long is an offsite, and what does it cost?
Most offsites run one to two days, working sessions a half day to a day. Around the room itself there is preparation the week before and a 30-day follow-through after, and those are where much of the value lives. Fees depend on scope, and we agree them on the discovery call once we both know what the room needs.
Facilitator or consultant: which do I need?
A consultant brings you an answer. A facilitator builds the answer with your team, so the team owns it. If your leadership team already has the knowledge but not the alignment, you want facilitation. I can flex between the two in the room, always labelled: process first, operator opinion when you ask for it. When it is a consultant you actually need, that work lives here.
How do you prepare?
One-on-one conversations with every seat in the room, so I walk in knowing where the real disagreements live. Where useful, a short assessment pass on personality, EQ and team dynamics. And a written outcome we agree in advance: what must be decided before the room empties.
Do you travel, and where are you based?
Based in Alpharetta, Georgia. I run sessions on-site anywhere in the country, and remotely when that fits the work. Atlanta metro in person is easy.
What happens after the session?
A 30-day follow-through. Decisions leave the room with owners and dates, and we check that the operating rhythm actually holds once the quarter starts pushing back. An offsite that only produces a good memory was a vacation.
Tell me about the room.
Forty-five minutes, no pressure, no pitch. Tell me what the session needs to produce and who will be in the room, and I will tell you honestly whether I am the right person to run it.
Or reach me directly:
(629) 304-8755
ken@kengavranovic.com