Leadership Move #27: Ask Probing Questions

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Sometimes it takes some digging to get to the root of things – and asking questions is a great way to do that.

But, not all questions are created equal.

  • Some questions are easy to answer but their answers provide little, if any, new insights.
    • Example: ‘Why’d ya do THAT?!’
    • The problem: Aside from the unavoidable judgment that will likely be in your tone, ‘why?’ questions, like these, tend to provide answers that are rarely of much help.
    • Better: ‘What did you learn for the next time?’ or some other question that encourages realizations and learning rather than excuses and justifications.
  • Some questions are easy to ask, but too hard to succinctly answer.
    • Example: ‘What specific steps did you take that resulted in this mess?’
    • The problem: In trying to get the details right, key insights are often lost or overlooked by both those explaining and listening to the explanation.
    • Better: ‘When did things start going sideways?’ or something that gets them to summarize the core issues of what they have to share.
  • Some questions make it too easy to get only part of the story – especially if you’re curiosity quotient is a bit low.
    • Example: ‘Did you address that customer issue I told you about?’
    • The problem: Closed-ended questions (ones that enables a yes- or no-type response) allow the person you’re asking to omit key information. You may get a definitive ‘yes’ or ‘no’ response, but you still won’t know what they did, when they did it, how well they did it, who they talked with, etc.
    • Better: ‘How did you address that customer issue I told you about?’ or another open-ended type question to allows you to know enough to speak knowledgeably about the matter.

Follow Up with Follow-Up Questions

It’s always best to assume that the first few questions you ask – whatever questions they are – will provide you with some, but definitely not all, of what you need, answer-wise. That’s why probing follow-up questions are so important. It’s in THEIR answers that the real insight and understanding reside.

Not sure what probing follow-up question to ask next? Try any one of these:

  • ‘What ELSE do you want to add to what you’ve told me so far?’
  • ‘What OTHER questions would it make sense for me to ask or for you to answer?’
  • ‘HOW do you want to proceed at this point, then?’

See what those questions do to improve the breadth and depth of the information you receive.


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Leadership Move #26: Explain the ‘Why?’

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Who hasn’t overheard this type of conversation between a boss and employee:

Boss: Do this.
Employee: Why?
Boss: Because I say so.

Given this reality, no wonder employee morale and engagement is so often as low as it is!

Sure, there are times when a crisis or tight deadline might require extreme employee responsiveness, but making them jump through hoops just because you can is bad form.

Why ‘Because I Say So ‘ is NOT Your Best Move

Sure, using these words can seem pretty effective.

  • They seem to save time.
  • They seem to eliminate the need to explain oneself.
  • And they seem to keeps things moving.

Or does they?

Initially, maybe yes. But you have to ask – whose time are you saving? And for how long? Because if you’re thinking that such heavy-handedness doesn’t result in considerable grousing about you behind your back, you’re terribly, terribly wrong.

And does it really eliminate the need to explain oneself? Maybe in this moment, but if your staff can’t figure out the rationale for your request, then they’re likely not going to be able to provide an end-product you’ll be satisfied with. No, chances are much better that they’ll only provide you with what you specifically asked for – what’s minimally required – rather than what you intended for them to do – or what would truly ‘wow!’ you.

As for it keeping things moving? Hardly. In truth, it’s actually far more likely that you’ll just end up creating one gigantic bottleneck as everyone around you simply learns that it’s best to just wait until you to tell them, precisely, what to do.

Besides, it’s just wrong for a boss to be that disrespectful.

Taking Time Saves Time

So is there a better way? Yes, there is: Whenever you have a task or assignment to delegate to someone, spend an extra 15 seconds and explain the ‘why?’ – the business justification – behind your request.

  • Why does the database needs to be scrubbed? Because inaccurate records delay our ability to respond to client concerns in an expeditious manner.
  • Why is the report now needed tomorrow? Because some important decisions need to be made and the report will provide the essential information we need to make them.
  • Why do we need stakeholder approval before this next step? Because while we can certainly wreck this project all by ourselves, the only way for it to succeed is with the support and involvement of our key business partners.

Getting clear on what the ‘why?’ (that is, the underlying business justification) isn’t always easy. But it is wildly important.


Why the ‘Why?’ Matters

Knowing, and being able to articulate the underlying ‘why?’ for everything you delegate makes it so much easier to talk in meaningful, relevant and compelling ways. And when your staff understands why it makes sense to be do what you’re asking them to, it becomes that much easier for them to do a better job.

Which makes employee buy-in that much easier.

Which moves things forward that much faster.

Which gives you, and others, much more time to work on what else is important.

Which makes it that much easier for you – and everyone else – to be notably successful.

Is ‘Because I Say So’ Ever Appropriate?

Not in those words, per se, no. But in times of true urgency, when you really do need extreme employee responsiveness, try saying this:

“I want you to know that there is a solid business justification for what I’m asking you to do, even if it’s unclear to you in this moment. And, while I’d be happy to explain the ‘why?’ to you later, if you’d like, because of the urgency of the matter, it’s essential that you take care of it, first, right now, without delay. Agreed?”

A Translucent ‘Why?’

But what if you don’t actually know (or can’t articulate) the ‘why?’ that you’ve been given by someone up the chain? What then? Well, perhaps that means you need to go ask your boss for some additional clarification.

And what if you don’t actually know (or can’t articulate) the ‘why?’ behind your own request? (Hey, it happens.) Well, perhaps – just perhaps – the task you had in mind really doesn’t need to be done, after all.

Hmm, not assigning unnecessary work? What a great way to improve employee morale and engagement!


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Leadership Move #25: Consider the Opposite Side of the Same Coin

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Decisions are like coins in that each decision has two immediate implications:

  1. What the decision allows or enables
  2. What the decision prevents or precludes

In other words, every ‘yes’ to one thing means a ‘no’ to something else.

So, when asked to make a decision – or to weigh in on an issue – consider BOTH sides of the coin, not just the one.

Some Examples

  • Data
    • Don’t just consider what data exists…
    • Consider what data is missing, as well.
  • Contracts
    • Don’t just read a contract for what it specifically says…
    • Read it for what it specifically omits, as well.
  • Approval Requests
    • Don’t just consider the implications of your approving something…
    • Consider the implications of your rejecting it, as well.
  • Momentum
    • Don’t just think in terms of what will move an initiative forward…
    • Think about what will prevent it from sliding backwards, as well.
  • People Management
    • Don’t just focus on what motivates people…
    • Consider how you may be inadvertently demotivating them, as well.
  • Matters Deserving Your Attention
    • Don’t just attend to problems…
    • Run with whatever opportunities present themselves to you, as well.
  • Teamwork
    • Don’t just consider what will make a team more engaged…
    • Consider what will make them more productive, as well…
  • Delegation
    • Don’t just delegate to your star players…
    • Delegate to your entire staff, as well.
  • Procedural Updates
    • Don’t just challenge procedures that you don’t like…
    • Challenge ones that your staff doesn’t like, as well.
  • Crises du Jou
    • Don’t just respond to what’s urgent…
    • Respond to what’s important, as well.

Get the picture?

One More Opposite-Side Benefit

Broadening how you make decisions and adjudicate issues, in this way, will not only improve the quality of YOUR decision-making, it will improve the decision-making of your staff, as well, as they notice, and emulate what you’re modeling for them.

And it’s exactly that type of leverage (1+1>2) that makes these Leadership Moves as powerful as they are.

Try them and see.

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