10 Questions to Ask Your Leader to Help Prioritize and Execute Projects

By Hallie Warner, Chief of Staff, AHC

One of the most important parts of being a strong strategic partner and invaluable Force Multiplier is understanding how your leader or Executive thinks and makes decisions. And because many of our leaders are visionaries and have brilliant ideas on the daily, it is also our responsibility to help them prioritize those ideas and determine which are the most important ones to act on and which ones can wait. So, while it would be nice to be able to read his or her mind, that’s just not possible. In lieu of mind-reading capabilities, you can get better at understanding your leader’s decision-making process with some key practices, and, of course, by asking really great questions.

Like many Force Multipliers, I am the Queen of Questions. I have an insatiable curiosity that I believe is necessary when leading alongside an Executive. Why? Because it helps drive clarity in the conversation, helps to prioritize projects, and ultimately, helps us all understand not only why we are making a decision, but who we will need to help execute, and how we’re going to get it done. One key component of leading up is challenging your Executive’s thinking and what better way to do that than by asking questions that help them see a different perspective and strengthen their thinking?

When I’m having these conversations with my leader I’m learning how he thinks, how he makes decisions, what information he is triangulating, how long does he wait before moving ahead, and more. I can help move that process along by having a series of questions at my fingertips. While it helps move the decision-making process along or helps clarify points for the rest of the team, it also is an excellent practice to help me hone my leadership skills and learn how my leader thinks and makes decisions, so I can be one step ahead in the future.

Here are 10 questions to ask your leader to help prioritize and execute projects:

1. Do you need some time to vent or do you want my questions/comments to help us formulate a solution? Vent? Okay, great, should we put a time limit on it? (Sometimes your leader just needs to have you listen. Make sure you are clear on what type of meeting you’re entering into before you start trying to solve all the problems).
2. Does this idea/project help serve our mission/vision/big why? Why is this important to you and the company?
3. Who will be leading this project? Who is responsible for the implementation?
4. Who will this impact? Do we need other parties’ input before we move forward? If so, who?
5. What is the desired outcome? What result are we looking for here?
6. What problem are we trying to solve? Is that the real problem or is there a bigger problem that we are ignoring?
7. When do you want this completed by? Why now? Does it have to happen this year?
8. Where does this project fit in based on XYZ annual initiatives? (Have a list of your company’s business plan or quarterly goals ready to go for all meetings!) Do we need to reset expectations on other projects to make this one happen?
9. How will we get this done? (This question I recommend you ask yourself, not your Executive, at least not right away. This is where I would suggest you ask for the time to process, and say something like, “Great info/idea. Is it alright if I process this information and come up with the HOW to make this happen based on what we talked about? I can have that back to you by Friday.” Your leaders should not be in the HOW meetings — that’s where you go plan/strategize/research and come back with a plan for execution, get their blessing, additional input, and then go forth and execute — often by leading through others — not always doing it yourself!)
10. What are we missing? What are we not considering or who are we not considering that we should be?

After you’ve asked the questions above and you’ve shared your perspective on the issues at hand, your leader will likely make a final decision. This is an opportunity to take your leadership to the next level by digging into their thinking and leadership style even more to really learn how they think. You can close the loop on their decision-making with the following:

• I want to learn how you make decisions.
• I want to make sure I understand how you are thinking and making decisions so I can better prepare information for you as we move forward.
• Could you explain to me your thinking behind that decision?
• Could you tell me what made you decide that/come to that final decision?

Getting to this place of discussion, dissent, and decision between a leader and a Force Multiplier is a process, but is ultimately what strategic partnerships are made of. You can fast-track building the relationship by holding weekly 1–1 meetings and implementing the 5 Daily Accountability Questions. Those two practices alone can help you both stay in sync and up to date on what decisions are being made and why. The more trust that is built (by following-through and over-delivering) then the more willing your Executive will be to not only share how they are thinking but to ask for your strategic counsel when making decisions. Especially, when you come prepared with powerful questions like the ones above.

Do you know how your leader thinks and makes decisions? What important questions would you add to this list?