10 Questions to Ask Your Leader

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Help prioritize and execute projects by asking your leader 10 questions says Hallie Warner

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 a daily basis, 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.

Be Curious

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?

Learn how your leader thinks

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 he waits 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.

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 plans 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.

Close the Loop on the Decision-Making Process

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?

A few other things to note

1. Be the truth teller

As a Force Multiplier, you are uniquely positioned to be that trusted adviser, confidante, and teller of truths to your Executive. They do not need a yes man or woman by their side, they usually have enough of those. What they need is someone to check them and to tell them what others won’t. Trust like this is built over time and as a Force Multiplier, you can get there faster by over-delivering on what you say you are going to do, maintaining the utmost confidentially and loyalty to your principal, and yes, by telling them hard truths when no one else will.

It is not about who is right or wrong, it is about seeing all truths and then finding the truth that aligns with the mission and vision and moving forward with clarity and purpose from that place of alignment. It is not always a comfortable place to be – telling the leader of an organization something that they might not want to hear.

However, I believe as Force Multiplier it is part of your responsibility and duty to your principal and the organization to do those hard things. I have had to bring several issues to Adam over the years that on the surface were not comfortable or particularly pleasant. But those feelings are short-lived and the outcome is always progress and growth.

2. Communicate the context

Visionaries are going to be visionaries, which by definition means thinking and planning for the future with imagination. Force Multipliers must help communicate the context of that vision to the right parties in the right way to ensure the message is heard and implemented. How? By getting extreme clarity from your principal, asking probing questions, challenging their thinking, and making sure you understand the direction of the organization.

It’s not enough to hear the vision or decision. That’s just the jumping off point. As a Force Multiplier, you need to understand the why, the decision making that went on behind the scenes, and the social, political, and economic implications of that decision. Only then can you fully understand the vision and message and carry it out throughout the organization on behalf of your principal.

One example of this in action is on the new podcast that Adam launched, called Business Meets Spirituality. I, too, am on that podcast from time to time, doing what I do best – asking questions! I may dig in deeper on an issue or give some background information on a particular topic to make the big ideas more digestible for our audience. Context is everything.

3. Never be indifferent and have a distinct viewpoint

It’s not only about asking great questions, but also knowing when to jump in and offer your advice and opinion as well. Remaining calm and unbiased is a critical skill for a Force Multiplier to develop in order to see an issue from all angles and present varying perspectives. But do not confuse neutral with indifferent. To develop as a strategic partner and leader, Force Multipliers must cultivate a viewpoint on challenges and share their thoughts (well researched, clear, and factual, of course) with their principal. Commitment (one way or the other) makes decision-making easier for everyone.

I have never lacked an opinion on any topic; indifference is not in my nature. When working through leadership challenges with my Executive, it is my responsibility to bring various perspectives to light, share which direction I think we should go in, challenge and disagree, and then commit. Once the decision has been made (whether or not I ultimately agree), I will support the decision and carry it out throughout the organization accordingly.

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 one-to-one 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.

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About Author

Hallie Warner

Hallie Warner serves as Chief of Staff to the Founder and CEO of Adam Hergenrother Companies. She is also the co-author of The Founder & The Force Multiplier: How Entrepreneurs and Executive Assistants Achieve More Together. Hallie has worked side-by-side with Adam Hergenrother for over nine years, ensuring that Adams vision is clarified, communicated, and executed. Hallie also provides strategic counsel to key leaders within the organization and leads special projects focused on the growth of the organization. In her free time, Hallie pursues her hobbies: reading, blogging, kayaking, and traveling, preferably to the beach. She lives in Vermont with her husband, Bill, and their dog, Karma.

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