‘Everyone has a plan until they get punched in the mouth.’
Mike Tyson wasn’t talking about transformation programs, but he could have been. Most plans look solid at the start. They’re logical, detailed, and confidently presented. The problem is that many aren’t built to survive the first punch.
Every program hits the messy middle.
That’s when the early excitement fades, delivery pressures ramp up, and reality starts to bite. Activities run late, dependencies aren't met and issues are raised. This is where even well-intentioned plans can start to wobble.
At Resulting IT, we focus on creating credible, realistic plans - plans that hold up in the messy middle, not just in a kick-off meeting. Here are 9 practical checks we often use to sense-check whether a plan is really fit for purpose.
1. Does the plan reflect how delivery actually feels? Early phases are usually fine. It’s the middle, when problems stack up, that really tests whether a plan is grounded in reality.
2. Are there clear stage gates or control points? Stage gates don’t need to be heavy or bureaucratic. At their best, they create clarity. They give teams a shared view of where they really are and create deliberate moments to decide whether to move forward, pause, or recalibrate.
3. Is everything in the past genuinely complete? This is one of the simplest, and most revealing checks. Look at the schedule and review everything that should already be finished. Are all tasks complete? Are dependencies genuinely met?
If there are still loose ends, that’s a big red flag. It usually means the foundations for the rest of the plan are being built on sand. People also tend to over-estimate their capacity to recover things and the impact will compound the further into a project we get.
4. Do different audiences get the right view of the plan? Not everyone needs the same level of detail. Senior stakeholders need a 'top-of-the-jigsaw-box' view. Are we on track, what milestones are approaching, what are the risks? They don’t need the nuts and bolts of a UAT testing schedule. Delivery teams do. At Resulting, we use standard planning levels to keep these views aligned.
5. Have you genuinely learned from the last time you did this? If similar projects ran late, or hit issues, has the learning shaped this plan? Or are the same assumptions being reused and we are at risk of repeating mistakes?
6. Are phases sequenced to set people up for success? We often see System Integration Testing (SIT) and User Acceptance Testing (UAT) overlapping to 'save time'. On paper, it looks sounds fine. In practice, it often causes problems. UAT teams are asked to validate something that isn’t stable yet.
It’s like trying to run a bath in a new house only to discover the pipes haven’t been connected. The bath is there. The taps are fitted. But no water comes out. A robust stage gate before starting UAT would help avoid this situation.
7. Are stage gates based on readiness, not just dates? Reaching a date doesn’t mean something is ready. Good stage gates focus on what needs to be true before you move on - criteria met, deliverables, evidence and confidence - not just the calendar.
8. Is the change work taken as seriously as the technical work? Training, Communications, Operations and Support often get squeezed when timelines are tight. But they matter just as much - especially in the messy middle, when confidence dips and you need everybody on board and pulling in the same direction.
9. Does the plan reflect real capacity? Assuming people can run flat out for months on end doesn't work. Credible plans acknowledge competing priorities, fatigue, and the reality of day jobs alongside change.
Good planning isn’t about predicting everything perfectly. It’s about being honest about progress, using stage gates to surface reality, and fixing weak foundations before moving forward.
At Resulting IT, we believe the best plans are the ones that survive the messy middle - because they’re grounded in experience, balanced between technology and change, and designed to set people up for success.
If you’d like to sense-check your program plan, get in touch - we’d love to help.