A challenging narrative I often hear in my executive coaching sessions is, “How do I handle my difficult boss/client?”

While there are many types and reasons for a person to be difficult, there’s at least one pattern which is common. Typically, the story plays out something like this.

Round 1
The difficult supervisor/client cuts you apart drilling endlessly into details. You discover that you failed to prepare a sufficient level of detail for the meeting and may have been exposed.

Round 2
Having been left unsettled by Round 1, you prepare ad nauseum for the next meeting. You’re determined that you’re not going to be told that you weren’t prepared. You’re nervous but ready to go with more detail than the supervisor/client could possibly ask for. You don’t make it 5 minutes into your presentation before he/she interrupts you and says something to the effect of, “I don’t want to get into all of these details.” You try to shift to high level, but your preparation was intently focused on the granular. You leave Round 2 as bruised as from Round 1.

What’s worse, you’re now left at a loss as to how to deal with this person. Do they want high-level or do they want details?

The truth of the matter is that these individuals want both! And yes, they want them pretty much at the same time!

The whole situation reminds me of growing up in the United States and celebrating the well known American holiday Thanksgiving. An essential part of the Thanksgiving meal is turkey. These turkeys are expected to be beautifully presented on the outside with a brown exterior. But they also must be fully cooked!

The dilemma at Thanksgiving time is, “How do you ensure the bird is fully cooked on the inside, without cutting it on the outside?” The answer? A meat thermometer.

A meat thermometer is a metal probe which a chef randomly inserts into the food being prepared to determine the internal temperature of whatever he/she is cooking. It is a way to test whether something is fully cooked without affecting the outside appearance.

When difficult bosses/clients randomly seem to “probe” us for details, they are doing the same thing. They don’t have time to get into every detail, but they do have a strong desire to know whether whatever we have prepared is “fully cooked.”

There are often two (opposing) factors. On the one hand, such individuals are often strongly outcome focused. Time is one of their most precious resources and they don’t want to “waste time” talking about things which (they deem) do not add value. On the other hand, they are not quick to extend trust, especially if what they are entrusting to us is important to them. When such individuals worked at more junior levels, they had sufficient time to personally ensure every detail under their purview was executed to perfection. Now that they hold senior levels of responsibility, time has become a luxury.

Part of them wants to hear bullet points so that they can drive outcomes as rapidly as possible. But the other part of them wants fine detail to be sure that nothing will go wrong.

The result? Random probing to test whether they can be sure that the entire package is “fully cooked.”
So, how do we manage such a person?

Here’s a several step process you might find helpful:

1. When you prepare, if the meeting requires a presentation deck, always prepare your information in two parts. The first part should be high-level, the big picture story. The second part is an appendix with all of the fine detail to ensure that you are fully prepared for the “probing.”
2. When you begin any meeting, always start with high level. Don’t deviate from that plan until the challenging stakeholder makes the shift to detail.
3. When you hear them ask for detail, change your gears as quickly as you can. Dive into the details of their question or comment, using the appendix slides if needed. And once you make that shift, give them the details.
4. If you’ve done your homework right and covered things in enough detail, eventually, you will hear them relent. You should eventually hear a note of (relative) satisfaction. When you hear them shift back to high-level, you will have to quickly shift gears again. Do not remain stuck in the fine-detail or they may become impatient.
5. Repeat as many times as necessary.

With stakeholders who know you to a lesser degree, it is normal to be “tested” three or four times in a meeting. If you pass those three or four tests, the next time you meet they are likely to probe you less because trust that your high-level statements are “fully cooked” will have started to form in their minds. In general, once you’ve established yourself, most meetings will reduce to one or two tests on the details. And eventually, in some cases, trust levels come to a place where they hardly probe at all.

So, the next time you face your challenging supervisor or client, give it a try to see if this works for you.