Dig Deeper When Asking “When?”

escavation-921233_640When bosses ask their direct reports for some type of deliverable, most employees respond by asking, “When do you need it by?” Grammar aside, it’s an important question, to be sure. But is it really the best question to ask? I’m not so sure.

Case-in-Point: I remember once asking one of my direct reports to update a PowerPoint deck for me. “When do you need it by?” she dutifully asked. By 2pm, I replied. Unfortunately (for me), she missed the deadline. Not by much (her email’s timestamp read 2:17pm) but what she didn’t know – and I take full responsibility for not telling her – was that I wanted the slides refreshed for a boardroom presentation I was scheduled to start at 2:15 pm, sharp. (And yes, I was asked why my data was as stale as it was.)

What I learned from that experience was that I needed to improve my delegation skills. Staff merely knowing WHEN something was due (by) – ☺ – was not enough. I wanted them to know WHY I was asking for it and HOW I intended to use it. That would not only improve the quality and timeliness of the information coming back to me, I felt, but would greatly simplify any back-end accountability discussions we might have later, be they developmental or congratulatory in nature.

The results were consistently strong – wonderfully so. So much so, that I starting asking, “How will you be using what I give you?” whenever my bosses gave me a new assignment. It became my automatic go-to question. The reasons were fourfold:

  1. To uncover the underlying ‘so that’ Every task every boss assigns has an implicit ‘so that’ in it. Please run the latest sales figures (so that I can prepare to discuss them with my own boss). Please run the latest sales figures (so that I can prepare to discuss them with my direct reports). Please run the latest sales figures (so that I can decide how much time I can spend at my beach house this summer). Same assignment, but decidedly different ‘so that’s.’Knowing the underlying ‘so that’ makes it so much easier to be that much more relevant and helpful. With respect to the sales figures request, knowing HOW the information will be used might encourage you to:
    • Include current quarter to prior quarter ratios (because you now know that your boss’ boss will be asking about them), or
    • Calculate the percent of total team sales that each salesperson’s results represents (because you now know your boss wants everyone to see their level of contribution), or
    • Highlight the region’s current pipeline estimates (because you now know that if the boss is going to take an extended vacation, this summer, he’ll want to make sure everyone is actively prospecting, beforehand).
  2. To uncover the level of detail needed – The CFO called and wanted my budget projections for the next 5 years…in 2 hours. It was a seemingly impossible task – I’d need more time just to revise my current year projections. My options seemed limited: Provide a sufficiently detailed estimate, late; or provide unjustifiable soft numbers, on time. I asked the CFO which he preferred. He reiterated that he wanted my numbers on time, which was no surprise, but what was a surprise was that, based on how he was going to use the information, he said if it helped, I could round my numbers to the nearest $10million. Indeed. My seeming awkward question turned an impossible assignment into a reasonable and doable one.
  3. To uncover the forum in which the information will be used – Simply stated, what an update for ‘internal use only’ should look like is materially different from one for a major presentation, or, as in the CFO’s case, one for a preliminary strategic planning session. It’s an essential bit of context that delegators often fail to disclose, unless asked.
  4. To uncover the assignment’s actual deadline – More often than not, a boss builds slack time into a delegated assignment’s due date. How much may vary, so understanding the broader timeline can be very helpful – especially if you need to negotiate a deadline. For example, if your boss wants something turned in first thing Thursday morning, but acknowledges that he won’t actually have time to look at it until Thursday afternoon, you’ve just potentially gained yourself an additional half-day. Similarly, if your boss says something is due by end-of-day Friday, so she’ll have it for a 730am meeting on Monday, you might be able to gain an extra two days, if you don’t mind working on it over the weekend. Know that there may not be any, or only limited, flexibility in a deadline, though. (She may want to use the weekend to study the materials you provide, although might be okay waiting until Saturday noon to start, if that helps any.) The point is, you’ll never know unless you ask. So ask; don’t assume.

That’s why, whenever you’re given a new assignment, I recommend you dig a little bit deeper. Don’t just ask when it’s due, ask, “How will you be using what I give you?”

P.S. What other questions have you found helpful to ask when your boss delegates something to you?

 

(Originally published as a LinkedIn post of mine on 5/21/2015 that was included in LinkedIn’s Pulse.)