Between Mondays

Author: Brad McKinney

Start With Their Picture of Success
The strongest collaborations do not start with a plan. They start with a question. What does success look like to you? It is a simple thing to ask and an easy thing to skip, and skipping it is where a lot of good projects quietly go wrong.

When we bring partners into a program, the instinct is to show up with the plan already shaped and ask them to help carry it. It feels like a good use of everyone’s time. The plan exists, it is reasonable, and walking someone through it feels like progress. But it skips the step that actually makes partnership work, which is understanding what winning looks like from where they sit.

What a partner’s current process is actually protecting

Partners who have run their own operations for years did not arrive at their current way of working by accident. It survived contact with real constraints:
- Budget cycles that do not line up with the program’s own timeline.
- Staffing realities that limit how much change they can absorb at once.
- Relationships with their own stakeholders, built over years, that a new plan can put at risk.
- Past efforts that failed for reasons nobody wrote down, and no one wants to repeat.
When a plan shows up without first asking about any of that, it reads as a demand instead of an invitation, even when nobody intended it that way — the same blind spot that makes an undocumented workaround look like a mistake instead of a reasonable adaptation.

A plan that skips their picture of success is not really a shared plan. It is your plan, waiting for their agreement.

What asking early actually buys you

Asking the question early does two things at once. It surfaces constraints early, while there is still time to design around them, instead of months later when a decision that felt final has to be unwound. And it signals something about the relationship itself: that this is being built together rather than delivered to them. That signal matters more than most schedules give it credit for. People commit differently to a plan they helped shape than to one they were handed.

As a director, this is one of the cheapest habits to adopt and one of the easiest to forget under deadline pressure. It takes one conversation, maybe two, before the plan is fully formed. What it buys in return is a partner who can tell you early when something will not work, instead of one who nods along and quietly routes around the plan later — the same slow, quiet erosion that makes a transformation feel stalled long after the real damage was done.

The picture of success a partner describes rarely matches the plan word for word. That gap is not a problem to smooth over. It is the actual starting point. Find it first, and the plan you build from there has a real chance of being one both sides actually want to see through.

More essays like this one live on the Between Mondays articles page.

Further reading: the Project Management Institute and Harvard Business Review both cover stakeholder alignment in more depth.
July 24, 2026
Why the Gaps You Find Are the Point
A few months into any process improvement effort, someone on the team says some version of the same thing. “I thought we all did it the same way.” Then it turns out three people on the same team handle the exact same task three different ways, and none of those ways match what the manual says, and none of them match what leadership thinks happens.

The instinct is to treat this as a problem. Somebody did not follow the process. Documentation is out of date. Training failed somewhere. All of that might be true. But there is a more useful way to think about it, one that comes out of safety and reliability research, not management theory.

Treat the gap as data, not a verdict

In that world, a gap between the documented process and the actual process is not treated as a failure. It is treated as data. It tells you where the written process does not match the conditions people are actually working in. Maybe the manual assumes a resource that is not always available. Maybe the “correct” way takes twice as long under real workload, so people quietly built a faster path that mostly works. Either way, the gap is information about the system, not a verdict on the person.

A process nobody actually follows is not a process. It is a suggestion with better formatting.

As a director, the instinct when you find one of these gaps is to close it immediately, tell everyone to follow the documented process, and move on. That instinct is usually wrong, or at least premature. Ask why the gap exists before deciding which side of it is right:
- Sometimes the documented process is correct and people drifted from it for reasons worth correcting.
- Just as often, the workaround people invented is the more honest description of how the work actually gets done, and the manual is the thing that needs to change.
What changes when gaps are safe to report

This reframe changes how a team responds when gaps surface. Instead of bracing for blame, people start bringing the gaps forward voluntarily, because they have seen that surfacing one leads to a better process rather than a harder conversation. That shift alone is worth more than any individual fix. A team that hides its workarounds cannot be improved. A team that surfaces them can — the same shift in posture that makes it possible to tell the truth plainly in a status update instead of dressing it up.

The goal was never for everyone to do it the same way for its own sake. The goal is for the way it gets done to actually work, to be known, and to be something the organization chose rather than something that accumulated by accident. Finding out three people do it three different ways is not the failure. Not finding out would have been — it is the same quiet blind spot that makes a transformation feel like it is stalling when it is actually just under-measured.

More essays like this one live on the Between Mondays articles page.

Further reading: OSHA and NIST both publish extensively on treating near-misses and process deviations as safety signal rather than blame.
July 24, 2026
The Story Behind the Decision
How we communicate complex work, and earn the trust to lead through it

There is a particular moment that shows up in every major technology program. Something has to be decided. Maybe the original plan no longer fits the reality on the ground. Maybe two paths forward exist and both carry risk. Maybe a deadline is slipping, a vendor relationship is strained, or a design assumption from months ago no longer holds. Whatever the trigger, the team has done the hard work of understanding the problem. Now the work shifts, and it shifts to communication.

How we tell the story surrounding that decision matters more than most people realize. Not because the truth needs to be dressed up or spun. But because leadership, the people with the authority and accountability to act, can only make good decisions when they clearly understand what they are deciding and why.

This is one of the most important skills a director can build. Not just for escalation moments, but every week, in every written update, status report, and hallway conversation. Much of the job is translating complex work into something that makes sense to people who are not living inside it every day — the same translation work that makes a slow-feeling transformation legible to the people funding it.

The team that can explain what it is doing, and why it matters, earns the credibility to keep doing it.

If anything, complexity is the reason we have to be more intentional about it. The more complex the work, the more important it is that the people responsible for the organization’s success can understand what is happening and why it matters.

Where updates usually go wrong

There is a version of this that goes wrong often enough to name directly. A team gets so close to a problem that it forgets what it sounded like before it understood it. The update comes out dense with acronyms and caveats, technically accurate and functionally useless to the person reading it. That person then makes a decision based on a headline instead of the substance, because the substance was never made available to them in a form they could use.

Three questions worth answering before the meeting

The fix is not to simplify the truth. It is to do the translation work before the meeting instead of during it:
1. What is the decision, in one sentence?
2. What are the real options, in plain terms?
3. What happens if we choose wrong?
A leader who can answer those three questions clearly has usually already done the hardest part of the job. It is the same discipline behind naming a process gap plainly instead of burying it — the gaps a team finds are the point, not something to explain away.

We have an obligation to meet people where they are. To translate. To simplify without being condescending. To tell the story around the decision, not just the decision itself. When we do that well, we do not just get better outcomes on the immediate issue. We build the kind of credibility that makes everything else easier.

More essays like this one live on the Between Mondays articles page.

Further reading: Harvard Business Review and the Project Management Institute both write regularly on communicating decisions under uncertainty.
July 24, 2026
Why Transformation Feels Slow
Most people expect change to feel like change. They imagine a clear before and after, a moment where the old way gives way to the new. What they get instead is months of meetings, miscommunication, and incremental progress that barely registers on a day-to-day basis. It can feel like nothing is working. Usually, everything is.

The trouble is that real transformation requires three things to shift at once, and each one moves at a different speed:
- Processes — the easiest to document, and the hardest to actually change once people have muscle memory built around the old way.
- Technology — needs configuring, integrating, testing, and retesting, and no system survives contact with reality without adjustments nobody budgeted time for.
- Culture — the slowest of the three. It shifts only through repetition and through leadership behaving consistently with the stated values, over and over, for a long time.
Together, these three create a pace that can look, from the outside, like stalling. Processes are the easiest to document and the hardest to change. People have muscle memory built around the old way. Even when they understand the new approach intellectually, their instinct is to fall back on what they know when things get busy or stressful. That is not resistance. That is just being human.

How to lead through the slow middle

A go-live date changes a system. It does not change a habit.

So progress tends to feel invisible for a while. Teams are learning. Systems are stabilizing. Habits are forming beneath the surface. And then something clicks. A team hits a milestone that felt impossible six months ago. A process that used to take three days takes three hours. People stop asking how the old system worked because they have genuinely stopped thinking about it.

As a director running programs like this, the hardest discipline is resisting the urge to manufacture a feeling of speed. It is tempting to add a dashboard, a new status color, a fresh set of metrics, just so the pace looks faster than it feels. None of that changes the underlying math. Three systems have to shift together, and none of them shift on command. It is the same discipline behind asking a partner what their picture of success looks like before handing them a plan — slowing down on purpose, in the moment it is least comfortable to do so.

What actually helps is naming the slowness out loud, early, before anyone starts to panic about it. Tell the team and the stakeholders: this will feel slower than it is. Explain why. Then keep pointing at the small, real signs of movement instead of waiting for one big moment that proves the change worked. Those moments rarely arrive on schedule. The quieter evidence is there the whole time, if you know where to look — often in the same unglamorous places a team’s process gaps turn out to hide it.

That is the shape of meaningful change. Getting the story right when you have to explain that pace to leadership is its own skill, one worth as much attention as the change itself.

More essays like this one live on the Between Mondays articles page.

Further reading: McKinsey on organizational transformation and the Project Management Institute both cover the mechanics of large-scale change in more depth.
July 24, 2026