The 2 questions I always ask: Part 2

Whenever I work with leaders (mostly Principals, Executive Directors, someone with Chief in their title, etc.), I think about two questions. I started to talk about this last week, where I zoomed in on the second question I usually ask myself: to what extent is their leadership team helping or hurting?


Today, I want to focus on the first question–which is first for a reason, as it’s the most important:


To what extent is this leader clear? 


What the leader needs to be clear on depends on the specific problems they are working to solve—if I’m working with a leader on resetting their leadership team, I’m considering how clear-eyed they are about the strengths and challenges facing them with the current team. If a leader wants to make their role as Principal or Executive Director more instructionally-focused, I think about their vision for what this means and how we can address the change management process.


Sometimes, though, leaders aren’t clear–and that’s okay.

Leadership means a million to-dos buzzing in your head, background noise about how that event across town is going and why that donor hasn’t gotten to me yet and the promising person you interviewed yesterday and so much more. There’s not always time, space, perspective and background knowledge to be able to come to the table with a clear vision.


When leaders come to me, they often have the beginning of an idea–much like Michaelangelo had a block of marble before he sculpted the David. For a variety of reasons, they know that <becoming more goal-focused as an organization, revamping the performance management system, working to embed growth mindset into their org culture> is important, and the right direction to take the organization in.


As we start talking, I’m asking myself the first question: To what extent is this leader clear? Almost simultaneously, I’m also considering the second question: to what extent is their leadership team helping or hurting? When it’s about an idea the leader wants to bring into fruition, I try to weigh: to what extent their team likely will help or likely will hurt getting that idea into reality. For example, sometimes it’s clear that a Deputy Director has a lot of fixed mindsets–and that may make it very likely that embedding more of a growth mindset in the culture may be more difficult because of the entrenched view of a senior leader.


My decades of experience as a senior leader myself means I deeply understand what it is like to sit in that seat, the myriad of challenges that a leader faces and the considerations when deciding when to act. So I know that by the time they’re talking with me about the idea of acting, they are serious about it.

Part of my job is to be a doula to their idea–to help them become more clear. It’s rare that people come in crystal clear on their vision–instead, they have an idea and they need help flushing it out, and it’s my role as a coach-sultant that helps them become more clear in their vision.

Clarity means having definite ideas about what will and what won’t be true, what a typical day looks/sounds/feels like, what weekly/monthly/annual routines and rituals will support this, and being able to easily explain the why, even when pushed with tough questions. That’s a tall order for an idea about something moving forward, which isn’t reality yet. Working with me means carving out dedicated time to get to their clarity–and often, in just a few meetings, we’re able to get from a fuzzy idea of what might be true to a totally clear vision. 

Then, once we have the clear vision, we can tackle the change management process and work to create a plan, and then implement it, so that that vision can become reality–the most rewarding part of any work I do!


So, leaders, if you’re feeling like, “I just don’t have total clarity on this yet, but I know it needs to happen”--think about bringing in an outside perspective. Making the investment both with your time and your resources means that time will be carved out on the calendar, you can bring someone in who has the benefit of a broad perspective on this issue across many organizations and by giving yourself the gifts of time to think and a thought partner, in weeks you can be 100 times more clear than you are today about this critical work that you know will help your organization and bring your vision closer to reality.


If you’re interested in exploring more about what this could look like, book a call today to see what this could look like.

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The 2 questions I always ask