Offsites and strategic planning sessions, run by an operator.
Updated September 2026
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.
Every room has its own stakes. A team that thinks it is aligned and needs to be sure. A team that knows it is not. A new team that has never made a hard decision together. A PE owner pressing on margin. A milestone the next round depends on. A do-or-die year on the road to an IPO. The agenda is never just the agenda, and a facilitator who has not lived those pressures cannot hear what your room is really negotiating.
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 and leadership 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.
Leadership alignment workshops
A half day to a day for a team that thinks it is aligned and needs to find out whether that is true. Same discipline as an offsite: the decisions written down first, disagreement surfaced early, and a log with owners and dates before anyone leaves.
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 method, in three parts.
People ask what my method is. It is the before, in the room, after discipline above, and it produces two artefacts you can ask any facilitator to show you: the decision list and the decision log.
Before the agenda exists, the CEO and I agree the decision list: a one-page list of the three to five decisions the team must make before the room empties. Each line names the decision, who owns it today, and what "decided" will look like when the room reads it back. It is not a list of topics. "Discuss pricing" is a topic. "Decide whether we raise list price in the first quarter, and by how much" is a decision. Each decision on the list has to be a must, with the where and the why attached, or it comes off the list. Once the list exists I talk with every seat in the room one on one, confidentially, for 45 to 60 minutes each, and the agenda comes out of what I hear, not out of a template.
In the room, two rules hold. Decision rights get named before the decision gets made: who decides, who gets a say, who has to live with it. Most alignment problems are unsettled decision rights wearing a disguise. And every decision is captured in the decision log as it happens: what was decided, what was deliberately deferred and until when, what was escalated, who owns it, and the first action with a date. Before the room empties I read the log back against the decision list. If they do not match, we are not done.
After, the decision log goes to every attendee within two business days, and the 30-day follow-through checks each owner and date against the operating rhythm the decisions plug into. The measure of an offsite is not the two days. It is the ninety after.
Further reading: Frisch and Chandler, "Off-Sites That Work" (HBR, 2006), and Rogers and Blenko, "Who Has the D?" (HBR, 2006).
The Decision Contract, on one page.
A Decision Contract is a one-page list of the three to five decisions the leadership team must make before the room empties, agreed in writing by the CEO and the facilitator before the agenda exists. Each line names the decision, who owns it today, what it costs to leave it open another quarter, and what "decided" will look like when the room reads it back. Here is the template I use. Fill it in before you book a room, with me or with anyone.
| # | The decision (a choice, not a topic) | Who owns it today | What it costs to leave it open another quarter | What "decided" will look like when read back |
|---|---|---|---|---|
| e.g. | Raise list price in Q1, and by how much | CRO, with CFO | About $1.2M of margin, and a pricing conversation at every board meeting | A number, an effective date, an owner for the customer message, and the first action dated |
| 1 | ||||
| 2 | ||||
| 3 | ||||
| 4 | ||||
| 5 |
Topics are not decisions. "Discuss pricing" is a topic. "Decide whether we raise list price in the first quarter, and by how much" is a decision. Each line has to be a must, with the where and the why attached, or it comes off the list.
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, CMHC graduate work 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. In-person executive offsites across Alpharetta and the Atlanta metro; on-site by engagement anywhere in the country. I work remotely with leaders everywhere. (629) 304-8755 · ken@kengavranovic.com
The ones people actually ask.
Is there a Decision Contract template I can use?
Yes. The one-page Decision Contract template, the executive offsite planning template I use, is on this page and as a PDF: the three to five decisions the offsite exists to make, who owns each today, what it costs to leave it open another quarter, and what "decided" will look like when the room reads it back. Fill it in before you book a room, with me or with anyone, and bring it to the discovery call.
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 do I choose an offsite facilitator?
Ask for three things. First, can they actually run a room. Trained, practiced, with the craft to make it safe to say the true thing. My rooms have ranged from Gartner and AWS re:Invent keynotes to customer events around the globe, to presenting to tough boards as the leader in the chair, to sitting on boards judging the plan. Twenty-five years of rooms, from both sides of the table. Second, have they lived your situation: the PE pressure, the funding milestone, the IPO year. I have sat in those seats, not next to them. Third, do they have the training to work the human side: a BS in Psychology, a master's in CMHC underway, and sessions that are assessment-informed when useful. The goal is not a good two days. It is a team that executes better and holds together after. If you are the chief of staff or the executive assistant building the shortlist, ask every candidate the same four questions. What is your method, and can you describe it in one paragraph? Have you held a seat like the ones in our room? Will you interview every attendee before the agenda is set? What do we receive after the room, and for how long? Then give the finalists the same real situation and compare the agendas they propose. Hire the one whose agenda starts with decisions rather than topics. The long version, with the method, is in How to Run an Executive Offsite That Actually Produces Decisions.
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.
Facilitator or team coach: which does your team need?
If your team knows what to do and cannot get it decided, you want a facilitator: a structured room, disagreement surfaced early, decisions that leave with owners and dates. If the same problem comes back every quarter, the pattern lives in how your team works, and that is standing work: leadership team coaching, which I do separately. One honest conversation usually tells you which it is, and I will tell you plainly, including when it is not me.
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. That written outcome is the Decision Contract, explained here.
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.
Who should be in the room?
The CEO and the direct reports who own the decisions on the list. Add a board member or an advisor for a specific block if one decision needs them. Do not add people because leaving them out would feel awkward. Every extra seat makes the true thing harder to say.
Can the CEO facilitate their own offsite?
Rarely well. The CEO is a party to every decision on the list and the person the room is most careful around. Whoever runs the process cannot also be in the argument, and the argument is the point.
Offsite, retreat, workshop, or alignment session: what is the difference?
The method is the same; the emphasis moves. An executive offsite is the one- or two-day room where a leadership team resets its plan. A leadership retreat or executive retreat puts the team itself on the agenda: trust, candour, how it handles disagreement, with the business decisions along for the ride. A leadership workshop is a half day to a day on one problem that will not die in email. A leadership alignment workshop is for a team that thinks it is aligned and needs to find out whether that is true. All four start with the decisions written down, because a retreat that builds trust and decides nothing does not hold either.
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