Sunday, March 17, 2019

Starting Work With a Difficult Stakeholder: First Steps

Updated September 2026: this 2019 post described being assigned, late on a Friday, an opportunity involving an onsite delivery person known for demanding endless updates, and the relief of a supportive offshore colleague. I have rewritten it into advice for the first days on work with a stakeholder who has a difficult reputation.

My manager assigned the opportunity late in the day. Reading through it, I saw the name of an onsite delivery person known for asking for many unnecessary changes, and my heart sank. The one comfort was an offshore delivery colleague I had not worked with before. I called him that evening to ask what was needed. He was calm and encouraging: little was needed until the client answered the questionnaire. I signed off for the weekend relieved.

Should you trust a colleague's reputation?

As a warning, not a verdict. Reputations tell you where friction has happened before, often around changing requirements or late requests. They do not tell you how the person will behave with you, on this piece of work. Prepare for the known pattern, but start neutral.

What should you do in the first days?

  • Call your closest collaborator early, as I did with the offshore colleague. Knowing what is actually needed now removes most of the anxiety.
  • Confirm scope and approvals in writing, especially who signs off the deliverable.
  • Agree how changes will be requested, ideally through one channel.
  • Find out what the client is waiting on, because nothing moves faster than the client's answers.

How do you handle a stakeholder who asks for many updates?

Log each request with its date and reason, and batch them where you can: "I will include these three changes in tomorrow's version." Batching reduces the constant stop-start, and the log shows everyone how the scope has grown. If a change conflicts with an earlier instruction, point to the earlier one and ask which should stand.

Why does a supportive colleague matter so much?

Because they share the load and the context. A good offshore partner can absorb some requests, confirm priorities and back you up when requirements shift. Invest in that relationship early: keep them informed, credit their help and make their work easier in return.

When should you raise concerns with your manager?

When a pattern appears in the work itself, not before. Going to your manager on day one with "this person is difficult" sounds like prejudging. Going in week two with a log of repeated changes and their effect on the timeline gives your manager something to act on.

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