It usually happens about an hour into our quarterly planning session at SABO IT. This is where the customer and the team agree on what will be delivered over the coming months.
The customer has presented their priorities. The team has broken them down into tasks and estimated the effort involved. Then the customer compares what the team can realistically deliver with their wish list — and the numbers do not add up.
The room falls silent. Everyone is waiting for someone to say it. Then someone speaks up: “This will not all fit into this quarter.” That someone is us, the project managers.
Nobody likes hearing that sentence. But we have learned that the things customers least want to hear are often the most valuable things we can say. Speaking uncomfortable truths is not a last resort for us. It is part of the job.
Anyone who has worked on a software project knows the watermelon: green on the outside, red on the inside. Every status report says “on track.” Every risk is “under control.” Then, two weeks before the deadline, everything is on fire.
This happens because bad news feels threatening. The service provider fears that admitting a problem could cost them the contract. The project manager hopes the team will still catch up. So the problem goes unspoken, week after week.
The customer pays the price. They lose exactly what they would have needed most: time to respond. By the time the truth comes out, only expensive options remain.
We say this every quarter. Customers bring more priorities to planning than a team can deliver. That is normal: their business does not revolve around our team’s capacity.
The easiest option would be to agree to everything and hope for the best. Instead, we show how much work the team can realistically take on and ask the customer to prioritize. The first few minutes are uncomfortable. Then it becomes the most useful conversation of the entire planning session. At the end of the quarter, the customer gets what we committed to, rather than half of what they had hoped for.
Our most recently completed quarter shows what this means in practice. We committed to 71 tasks and delivered 69. One task was no longer needed; another is still open. During the same quarter, 12 new requests came in. We addressed four immediately, including a security incident. The other eight had to wait, rather than being squeezed in at the expense of work we had already committed to.
A new task arrives with a one-line description, no clear definition of when it is “done,” and an urgent deadline. We could simply start and clarify the rest as we go. We know how that ends: two weeks of work, a first look at the result, and then the customer says, “That is not what we meant.”
So we say no — but only to starting without a clear goal. We sit down with the customer, agree on what “done” means, and schedule the task for the next two-week cycle. At first, this feels like a delay. In practice, it is the fastest route to the right result, and the least expensive, because we avoid dead ends.
Budgets rarely run out all at once. They shrink week by week until, one day, the numbers no longer add up. When we see it coming, we say so early: at the current rate, the remaining budget will not cover all the planned tasks.
This is an uncomfortable message, especially when the customer has to pass it on to their own management. If it comes months in advance, there are still options: reprioritize, extend, or cut back. If it comes late, it becomes a problem.
That is why we reconcile the budget with the work actually performed every two weeks, rather than just once a quarter. One of our teams has worked around 2,300 man-days over the past two years. The difference between what the customer ordered and what we delivered is seven man-days — approximately 0.3%.
We tell customers when adding people will not make the team faster because onboarding initially slows everyone down. We also tell them when a feature is not worth developing, even if it would mean billable work. And if we reduce the scope of testing to meet a deadline, the customer hears that from us too. The risk then becomes a conscious, shared decision rather than a surprise in production.
Saying uncomfortable things is easy. Saying them in a way that actually helps is the real skill. We follow three rules.
Tell them early. Bad news have a shelf life. The same message that gives a customer room to maneuver in week two can back them into a corner in week ten.
Bring the numbers. “I have a really bad feeling about this” sparks a debate. Facts open up a conversation about how much the team can deliver, how quickly it is actually delivering, and how much work remains. With the numbers on the table, the customer sees what we see.
Never bring just a problem. Every difficult message needs at least one way forward: reduce the scope, change the order, or identify a decision we need from the customer.
This may sound contradictory at first. Customers trust us precisely because we tell them what they do not want to hear. Customers who know we raise problems also believe us when we say everything is on track. With us, a green status means green. That allows the customer to plan, make commitments to their own management, and avoid having to double-check our work.
Over time, the working relationship changes. A supplier who needs to be managed becomes a partner who works with the customer to find solutions. In our experience, this is how a single project becomes a long-term partnership.
One of our customer relationships shows how this works. It began several years ago, and two years ago we were working on a single project for this customer. Today, we manage six projects in parallel and deliver more than four times as much work as we did then.
We do not pretend this comes naturally. Nobody likes being the person whose words make the room fall silent. A quiet voice always says: wait another week; perhaps the team will catch up.
And sometimes we are wrong. A risk we flagged never materializes. Or the customer knows something about their priorities that we did not know. When that happens, we are just as open about it. Openness only works both ways.
If you work with an external team, think back over the past few months. Has your service provider ever told you something you did not want to hear? If not, it is worth asking what they have not told you.
And if you would prefer to hear it early, talk to us.
