A few weeks in, something the document didn't account for shows up, like a supplier missing a date or a hire falling through, and every plan meets something of that kind eventually.
What decides whether your organization keeps moving is whether the planning produced these five things.
1
When the chosen path stalls, your team has no idea what the alternatives were or why they lost, so they start from nothing.
2
Nobody notices when one of them stops being true, because nobody knew the plan depended on it.
3
The first surprise becomes a meeting about what to do, instead of somebody doing it.
4
Work waits at the edges between departments while each side assumes the other is moving.
5
Your people escalate things they could have settled, and settle things they should have escalated, and both cost you
Planning that produces those five things gives your leaders what they need to keep the work moving when conditions change.
Building more than one way to reach the objective, and comparing them honestly.
Saying out loud what you're assuming.
Finding what could go wrong while there's still time to decide what you'd do about it.
Agreeing where work moves between teams.
Settling who can decide what once the work is live
Recognize which assumption just stopped being true.
Reach for what was considered instead, and know why it lost.
Act on the contingency the team already agreed.
Know whether this one is theirs to settle or yours.
Keep the work moving without waiting for a meeting.
The plan on the page gets edited, and the objective still gets delivered.
Military planning exists to produce people who can keep acting once conditions change, so every assumption gets labelled, every risk gets a response, every handoff gets a signal, and everyone knows what they can decide without asking first.
Kyle Anderson, our co-founder, planned this way in Tier 1 Special Operations and brought the process into LoyaltyOps. We adapted it for the objectives a leadership team is working on and the pace of a growing organization.
Define the objective before designing anything.
Build two or three separate, complete routes to the same objective.
Walk the plan through live before the work starts.
Work inside time limits, so the thinking stays sharp.
Decide once, and commit.
Your leadership team agrees on the objective, the limits, and what good looks like.
An objective your team can repeat back without you.
Everyone hears that same framing together, in the same room, at the same time.
One shared starting point.
Small teams work separately, and each one builds a course of action to achieve the objective with its own assumptions, risks and trade-offs.
Real alternatives you can compare.
Each team presents its course of action, and you pick one and explain the reasoning in front of everyone.
A decision that holds, because the reasoning is public.
The people closest to the detail test the assumptions and close the gaps in the chosen route.
A plan your team can actually execute.
Your team walks the plan phase by phase and settles who owns each part, where the handoffs are, and who decides what.
Every part of the plan has a name against it.
Your team rehearses the plan in sequence before any work starts, testing the timing and each handoff.
Confusion found early, while it still costs nothing.
Once the work is done, your team compares what was meant to happen with what did, and works out why they differed and what they learned.
Planning that improves the team behind it.
When something changes, your people adjust and keep going, because they know what the plan was built on.
Problems get handled instead of scheduled, because the response was already decided.
Work stops waiting at the handoffs between teams, because each one has an owner and a signal.
Decisions that your leaders could have made stop coming back to you, and the ones that should reach you arrive sooner.
Decisions stay decided, because everyone heard the reasoning when it was made.
Your leaders plan this way on their own next time, and the planning gets better each round.
You write the plan, and the first time something changes, everyone waits for you to say what happens next. In this workshop, you learn a planning process you can use for any objective, built by the people who have to deliver it.
Best for organizations putting a group of leaders through development, or a leadership team that wants to learn the method before committing to the full engagement, at any group size, either virtually or onsite.
Your leaders run a condensed version of the process on a scenario, with competing teams, and finish with a decision and a debrief on how they worked. They practice every step and learn how their team plans under time pressure, while the outcome remains a training exercise.
Best for leaders who want a day that builds the team and teaches something they can use the following week, at any group size, working in teams, either virtually or onsite.
Day one teaches your team the planning process in detail. Day two runs the process through a scenario, all the way through to ownership and rehearsal. Leaders learn and can make mistakes with nothing at risk.
Best for a leadership team that wants to build stronger planning capability. Best with 9 to 15 people in the room. Always onsite.
We facilitate the planning process for your objective and maintain discipline while your team does the planning. Strategic planning, annual planning, quarterly planning, or any plan that is a high priority.
Best for leadership teams with a major objective who want expert support through the planning process. Annual planning, quarterly planning, or a high-stakes decision.
You have a major objective ahead, and you want your leadership team to own the plan for it.
Work that crosses departments keeps stalling at the handoffs between them.
Too much comes back to you that your leaders could settle themselves.
Last year's plan stopped working early, and your team waited for direction while it did.
Decisions get made and then reopened, and nobody can quite say who decided.
Your leaders are ready to think together, and the way they plan hasn't kept up with what you're asking of them.
Strategic planning settles what your organization is going to do, and this is about how your leaders plan whatever they’re planning, and what that planning leaves them with once the work is live. Teams use the process on annual plans, on a market entry, on a system migration, and on a problem that has to be solved in a hurry.
No. Your leadership team frames the objective, your teams build the routes, and your decision-maker chooses, while we hold the process, the phase boundaries and the time. We’re a leadership development firm, and the value here sits in how your organization thinks its way to a decision, which is work your own people are better placed to do.
Whoever makes the final decision needs to be there for both days, along with your executive leadership team, the functional leaders who would own parts of the plan, and a few of the people whose delivery experience you trust. Nine to fifteen works best, because the teams building routes need to be small enough that everyone in them is working.
The two days is always onsite, because the process depends on teams working in parallel in separate rooms and then briefing each other, and that falls apart over video. Workshops and team building sessions work well virtually.
Your team keeps the process, the templates and the phase checklists, and most teams run it themselves on the next objective. Some ask us back to facilitate when the objective is a large one, and that’s a facilitated planning session.
Your leaders spend the day on a real planning problem in competing teams, so what they learn about each other comes out of working under time pressure together, and they leave with a method they can use the following week.
On the call we'll look at the objective your organization is planning for, work out which format fits your leadership team, and agree whether this is the right next step.
LoyaltyOps™ HQ
430 Hazeldean Road,
Unit #6, Suite 17
Kanata, Ontario, Canada
K2L 1T9
Email: [email protected]
Phone: 1 365-659-4720
Copyright 2025 LoyaltyOps Inc. All Rights Reserved

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