Setting the right expectations is important is the first and most important step to success.

Over optimism is a sure way to sabotage the best investments, most accurate timelines and delivery of the intended outcome. And since estimation is the bedrock of planning and expectation setting, it’s a strength worth investing in.

I recall a week last summer when I helped different clients through a couple of project sessions; one a project launch that I lead, the other a retrospective which I had been asked to attend as an observer. The projects were remarkably similar. I made a mental note at the time to compare the outcomes. Now that the second has concluded, here are my observations.

The retrospective had been scheduled because the completed project had exceeded timeline estimates by 50%. Compromises had been made to wrap up at that point, and the shortcuts were continuing to drag on the business. There was a mood of disappointment. After listening to the roundtable discussion of outcomes, I asked the team to describe their project launch process. Turns out that the sponsors had spent 4 hours preparing the business case and timeline estimates, and reckoned on a 6-month timeline. That became 9-months, and the pressure had mounted during the overrun.

The new project launch brought 8 stakeholders and contributors together over 2-days. During this time, we crystalized the project goals and made 27 key decisions. We tested use cases, shortlisted essential outcomes, mitigated risks, and developed a plan for benefits realization. The group had confidence in the plan they had built. A year on, we conducted a retrosprective. The team delivered on the timeline, despite a couple of curve balls in their marketplace, and the benefits now being realized are 15% better than expected.

Here’s the thing …



My clients’ take-aways were:

  1. Good estimation drives great expectation setting, which gives the team room to succeed.

  2. Successful planning requires an environment that promotes candor and preparation.

  3. Experience counts most at the outset of any project; posing the right questions, examining the work to be done, challenging assumptions and mitigating risk.

  4. Breaking the work into smaller chunks is the best way to chip away at uncertainty.

  5. Be clear where the risks lie and develop mitigation strategies to counter them.

  6. Enumerate assumptions and adjust during the project if things change.

  7. Things change.

  8. If we are repeating work which is similar to projects we’ve done before, we have a benchmark to build on and can apply lessons learned. We can then focus on what’s different this time around and adjust our previous plans to accommodate the new.

  9. It’s harder to estimate work that is different from anything the organization has done before. We need to talk to someone who’s been there and done that. If they have the ability to quickly adapt their experience to our context, get them on the team, even if only in an advisory capacity.

  10. A “good” estimate pegs cost, effort and timeline within +/- 15%. We should plan for the upper bound and deliver within that budget.

  11. Always conduct a retrospective, whether the outcome is good or bad.

In short, businesses run better without unpleasant surprises, great expectations are laudable, and we all like happy endings.


Consider a major initiative where the outcome wasn’t everything you had hoped for:

  1. How happy were you with the estimates going in? Did you conduct a Discovery exercise?

  2. Was the team forced to take shortcuts when time was running out?

  3. Was quality compromised? How much repair or rework was required?

  4. When did the project really complete? Was the original intent fully achieved?

If you would like to discuss the outcome of this challenge, contact me at graham@primeFusion.ca.

The odds are good that I have been there, done that – or know someone who has!

… and if you missed these related articles, go back and take another look:

Revealing Value, one step at a time
Minimal Effort Means Avoiding Work
The most constructive question you can ask