The 10 Questions Great Leadership Teams Never Stop Asking

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Mike:

Most leadership teams think they need better answers, but the best teams focus on generating better questions. 

I just worked with a client earlier this week actually and did an exercise with them that I call personal development coaching, where I break them into diads or triads and they get to coach each other on some.

Challenge they’re having. But the ranks I throw into the mix is during the coaching, they’re not allowed to ask, they’re not allowed to give advice. They’re not allowed to make statements. They’re only allowed to ask questions. And the funny part of that is, I give them 10 minutes to coach each other and they think 10 minutes is just not enough time to add real value.

And what they find is number one. For some of them, after two minutes they run out of questions ’cause they’re not very good at what questions to ask. But once they start to get better at asking questions, they realize how much they could really accomplish by just asking great questions for about 10 minutes.

And, you know, the questions drive curiosity and new ideas. The questions teach and model away. for people to think. So really powerful to do that, to help people improve, to help people understand what coaching is versus giving advice. 

But what I wanna talk about in this episodes, on, in this episode is 10 questions that great leadership teams should never stop asking.

Not necessarily for just one-on-one coaching. In fact, the 10 questions that we’re gonna talk about are questions that are typically gonna be focused on the leadership team as a group. And I’m gonna talk about what those questions are. I’m gonna cluster them into to a few groupings and talk a little bit about where they go.

In the process, which of those questions, which questions should you be asking? You know, annually? Which questions should you be asking yourselves as a leadership team? Quarterly or monthly, or weekly? These 10 questions are not a one time exercise. Think of the more as a leadership operating systems. the complexity and speed of change today, especially with everything going on with ai, with everything going on in the world, answers get stale fast.

Solutions get stale, fast questions, never get old. Asking the right questions is always going to be relevant given where you are right now. Questions, keep the team curious, keep the team honest, keep the team adaptable. So let me just dive in to the 10 questions and the first couple questions. 

We’re gonna focus within a theme that I’ll just call direction and focus. First question.

What are the three to five things that are truly most important this quarter? In fact, I may modify that to say what are the two to three things that are truly most important this quarter? If everything’s a priority, nothing is a priority. We need to understand, we need to communicate, we need to live by as a leadership team.

The 2, 3, 4 most important things. That are important this quarter. what it reveals. The answer to that question reveals whether a leadership team is genuinely aligned around a short list of critical priorities. If you ask that question, what are the three things that are truly most important this quarter?

If different leaders answer with different things, if you get very siloed answers versus company answers, it says. We’re not aligned. it says we may not have clarity around what winning looks like for the next 90 days, where that question belongs in our rhythm of meetings. This question of what are the three things that are truly most important this quarter?

That’s a question kind of obvious from the question you should be asking quarterly. You should be asking in an annual. Planning session, I believe you should be asking in monthly check-in meetings as well. Just because you decide in a quarterly planning exercise, these are the three most important things for the company.

Doesn’t mean the world’s not gonna change within that quarter. So in monthly check-ins, hey, are we still focused on those three things that are most important? So that’s question number one. 

Question number two, still within this theme of direction and focus is what do we need to say no to in order to honor those priorities?

It’s real easy to say yes. It’s real hard to say no. There may be a dozen things or a hundred things we’re working on that don’t align with what those three most important things are. The easy thing to do is to keep working on those because there’s already momentum because last quarter or last month, we believed they were most important.

What this question reveals is whether the leadership team is willing to make trade-offs instead of trying to do everything it reveals whether scope is being managed or new priorities keep. Creeping in. Where that question of, you know, what must we say no to in order to honor these priorities? you know, that belongs certainly annually and quarterly.

That’s a great question, but revisiting that monthly is super important because it’s within the quarter that scope creep. Starts happening. So if monthly we’re asking the question, what do we need to say no to honor our top priorities? it helps scope creep from keeping it. So those are two, two great questions to ask, not the only questions to ask, but two great questions to ask around this theme of direction and focus.

The next theme is talent and team health. And there are three questions here. Number one. 

And our third of 10 questions is, are our best people working, and on our biggest and most important priorities? what it reveals is whether talent within your organization is being deployed strategically, or are we just filling seats?

Is there a misalignment between high performing team members and high impact roles or high impact projects? Where does that belong in, in the rhythm of meetings? Um, quarterly is a great time for that question. It’s a great tie in if you’ve listened to other,you know, other episodes of this podcast, if you’ve read my books, breakthrough Leadership Team and or The Strength of Talent, and of course you’ve read both of them, and if you haven’t, shame on you.

it, this is a, you know. Pretty, a great question. That ties into the quarterly talent assessment meeting, you know, every quarter assessing how are our direct reports doing? Who are our high performing team members, medium performing, low producing, low culture fit? That’s a great time to say. Let’s take a look at our high performing folks.

Do we have them aligned with our biggest opportunities, our most important projects or initiatives? 

Second question within the talent and health theme, but our fourth question overall is where are we tolerating low performing team members that are high performing team members see every day? and what that reveals are areas where low performing team members, whether they are low from a productivity standpoint or low from a culture fit standpoint, or maybe both.

It. It reveals the areas where low performing team members are dragging down the culture are dragging down productivity. it reveals whether the leadership team and the leaders are avoiding the tough conversations and the tough people decisions. It reveals where you might have some risk that your high performing folks will get fed up.

And go somewhere else. Go to grow somewhere else. Where does this one belong in the rhythm? again, that quarterly is a great time to ask this question. Where are we tolerating low performing team members that our high performing team members see every day? Quarterly, during that quarterly talent assessment that I mentioned in the last question and then.

the fifth question overall, the third question within this talent and team health, theme is who on this team needs more challenge and growth? In the next 90 days. And when you think about challenge and growth, you might think about low or medium performing, team members needing more growth.

But really my focus here is on your superstars. My focus here is on leveraging your highest performing team members. Remember, you don’t. You don’t create greatness. by. By maximizing weakness, you create greatness by maximizing strength. So where do you have high performing folks that are doing great, but you could challenge them and help them grow.

If they don’t grow with you, they’re gonna grow with someone else. So who on the team needs more challenge and more growth in the next 90 days? It reveals whether you’re high performing and high potential team members are getting stretch development , visibility. Um, is the team proactively growing, future leaders or just hoping somehow they’re gonna develop themselves?

Where does this belong in the rhythm? Again, quarterly is a great time to ask this question. During the quarterly talent assessment, meeting monthly is also a great time to, to ask this question. it’s a key driver. I just, did an episode that if you’re istening to this in order, may have been,Two or three weeks, ago. but it was recent called the 90 Day Talent Sprint. this is a key driver in that 90 day talent sprint. 

The third theme, and we’re up to the sixth question. Sorry for all the numbers, don’t mean to confuse you. The third theme is execution and accountability, and there are two questions there.

the first question and our sixth question overall is, where are we consistently dropping the ball and why? What it reveals are recurring breakdowns in process, in communication, in ownership, in accountability, it reveals whether issues are systemic, whether they’re rooted in a bad process, or whether they’re performance related, or they rooted in people that aren’t a good fit.

Best time to ask this is monthly. This is gonna help illuminate process issues, people issues, which are great topics for a monthly check-in meeting where part of your goal is to better understand and identify issues and opportunities.

The seventh question or the second question in this execution and accountability theme is what decisions have we made that we haven’t really acted on? What this one reveals is the gap between what gets said in meetings. And what actually gets done. How often, two months after you thought you made a decision, do you go back and say, Hey, whatever happened with that?

And everybody kind of looks at each other confused. It reveals whether the team has a culture of real follow through and real accountability, or is it just decision theater where belongs in the rhythm is weekly or monthly? It keeps the team honest about execution. It keeps the team honest about holding each other accountable to doing those things the individuals on the team have committed to do.

The last theme of questions, and there are three questions here, is culture and courage. 

The first question and our eighth question overall is what are we pretending not to know? I love that question, and by the way, very often at the very beginning of a meeting, after good news, I like to start monthly, quarterly, annual, even weekly meetings with good news.

For the monthly, quarterly, and annual. When you get a little bit more time, I like to have what I call pulse check questions at the beginning of the meeting. These are all amazing pulse check questions very often in a monthly, quarterly and annual meeting, you have an agenda, but the most important things are not on that agenda.

They come out of these pulse check questions and this idea of this question of what are we pretending not to know? It’s an amazing. Pulse check question. What it reveals are hidden truths that the team is avoiding brutal facts about people, about markets, about strategy, areas where fear, comfort, politics are blocking honest conversation very often teams are not great at.

Entering into conflict and having the difficult conversations and challenging each other. These types of questions give you practice in doing that. You may not be great right away, but this idea of what are we pretending not to know is so powerful? Where does it belong in the rhythm? Quarterly. Quarterly meetings are a great time.

and it ties to this idea of,of creating a vulnerability based trust kind of culture within your organization, a culture and an environment on the team where you’re willing to have that real difficult, sometimes scary conversation. 

Second question within this theme of culture and courage and the ninth question overall is, where are we playing it safe?

When we should be playing it bold? What that question reveals are opportunities where the team or the company might be underplaying due to risk aversion. Or due to complacency, it reveals whether the current strategy is ambitious enough for the company’s potential. Your highest performing team members want bold strategies, ambition ambitious strategies.

If your strategy is gonna get you to a 3 to 5% a year growth, you’re gonna lose your best people. Because if they’re not growing and getting challenged with you, they’re gonna grow with someone else. You’re gonna have a difficult time attracting great people. ’cause great people wanna go somewhere where they’re gonna be challenged, where the company’s gonna grow, where there’s more opportunity, where they can get paid some more because the company is earning more superstars.

Love the bold stuff. So the question of where are we playing it safe, where we should be bold is gonna challenge you as a leadership team to move faster and more aggressively on opportunities and with things moving as fast as they’re moving today. Speed is so critical. The days of saying, we’re gonna, you know, we’ve got this new opportunity, we’re gonna plan for the next three months, and then we’re gonna design what we’re gonna do and then we’re gonna execute.

The world has passed you by. You’ve gotta go do, where are we playing it safe when we should be being bold? That’s question number nine, and where does that fit, by the way? Where does that belong in the rhythm? That’s a great question to ask in annual planning to make sure you’re developing bold strategies for the years to come.

It’s a great question to ask. Quarterly planning, just a great one for strategy and innovation type discussions. And then question number 10. 

The third question within this theme of culture and courage is if we continue leading this way for the next three years, what kind of company will we create? If we continue leading this way for the next three years, what kind of company will we create?

What that reveals is the long-term impact of the current behaviors, the current culture, the current decisions that you’re making as a team, as a leadership team. It reveals whether there’s alignment or misalignment between today’s habits and the desired future state of. The organization such a powerful question that might reveal you are on the right track, very often reveals there’s some real opportunities.

To change behavior, change culture, change some of your decision making. This one is a great question to ask. During an annual planning retreat, it ties so directly to a three year vision set of work you’re gonna be doing and leadership self-awareness. 

So let me summarize how all this fits into your rhythm.

When you think about your annual planning retreats there, we want those big picture, future oriented questions. Questions like, where are we playing it safe? When we should be being bold. Questions like, if we continue leading this way for the next three years, what kind of company will we create in your quarterly planning meetings?

We wanna focus on priorities, talent, tough truths with each other. Questions like, what are the three things that are truly most important this quarter? Are our best people working on our biggest priorities? Where are we tolerating low performing team members, and what are we pretending not to know?

Monthly. In your monthly in meetings there, you wanna focus on execution gaps, decisions, alignment checks, questions like What must we say no to in order to honor our top priorities? Where are we consistently dropping the ball and why? Who on this team needs more challenge and growth in the next 90 days?

What decisions have we made that we haven’t really acted on? And then weekly, it’s about short, sharp. Prompts tied to, to live issues going on. What are we pretending not to know about this week? What decisions from last week have we not moved forward on? Lot of questions there. 

Hopefully you were able to pick a few or more than a few that are relevant.

You may not use them all at once , but my ask , my coaching to you is pick one. You might start asking weekly. Pick one that you might start asking monthly, one that you might start asking quarterly. Just start there and notice by asking those powerful questions how the quality of conversations and decision making on your team changes over time.

Great leadership teams are defined by the questions they never stop asking. If you want a great company, you need a great leadership team. I hope these questions got you closer there today. Talk to you soon. 

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