How can assistants help teams prioritize and accomplish projects? They need to get into the leader’s head. Here are 10 questions your assistant can ask to help prioritize and execute projects

We know how important it is to hire an assistant. As I mentioned in my article last week, “The first, and arguably the most important, hire you should make as a real estate agent or entrepreneur is an assistant. It’s your first point of leverage.” 

This hire allows you to start working in your strength zone and on the 20 percent of tasks that most impact the bottom line of your business. If you aren’t sure about hiring an assistant, don’t hesitate. An excellent assistant will force multiply your activities and the business

And, if you’re wondering why anyone would want to be your assistant, just know that being an assistant is not a stepping stone to another position, but rather it’s a dynamic and fulfilling career all on its own. Entrepreneurs and real estate professionals like you and I might not have chosen that career path, but as of 2019, there are over 500,000 individuals who did.

It’s a massive career opportunity. It’s the chance for force multipliers (assistants) to work alongside and learn from a successful Realtor and entrepreneur while using all of their skills, experience, leadership, resourcefulness, problem-solving, and strategic thinking abilities. What could be better than that? For both of you? 

Once you’ve made that hire and solidified the partnership, it’s time to keep growing. 

One of the most essential parts of being a strong strategic partner and invaluable assistant is understanding how your leader thinks and makes decisions. Many leaders are visionaries and have brilliant ideas on the daily. It’s the assistant’s responsibility to help prioritize those ideas and determine which are the most essential and which ones can wait. 

Although it would be nice for our assistants to read our minds, that’s just not possible. In lieu of mind-reading capabilities, assistants can better understand our decision-making process with some critical practices and, of course, by asking great questions.

My chief of staff and force multiplier, Hallie, is the queen of questions. She has an insatiable curiosity that definitely helps her work alongside me. Why? Because it helps to drive clarity in the conversation and prioritize projects. Ultimately, it helps us all understand why we are making a decision, who we will need to help execute it and how we’re going to get it done. 

One key component of an assistant’s job is challenging the leader’s thinking, and there’s no better way to do that than by asking questions. Questions that help team leaders see a different perspective and strengthen their thinking. 

When Hallie and I are having these conversations, she is able to learn how I think, how I make decisions, what information I am triangulating, how long I will wait before moving ahead and more. She can help move that process along by having a series of questions at her fingertips. 

It helps move the decision-making process along or helps clarify points for the rest of the team, and it’s also an excellent practice to help her hone her leadership skills and learn how I think and make decisions so that she can be one step ahead in the future.

10 questions to help prioritize and execute projects

We’ve put quite a bit of thought into this between our book and our blog, and we wanted to share our findings with you. Here are 10 questions your assistant can ask you to help prioritize and execute projects:

  1. Do you need some time to vent, or do you want my questions or comments to help us formulate a solution? Vent? Okay, great, should we put a time limit on it? (Sometimes, you just need someone to listen. Make sure you are both clear on what type of meeting you’re in before the questions begin). 
  2. Does this idea or project help serve our mission, vision or 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, whose? 
  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. By when do you want this completed? Why now? Does it have to happen this year?
  8. Where does this project fit in based on XYZ annual initiatives? (Your assistant should 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 your assistant asks himself or herself and not you, at least not right away. This is where I would suggest the assistant asks 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.” Leaders should not be in the how meetings — that’s where assistants go plan, strategize, research and come back with an execution plan, get the leader’s blessing, additional input, and then go forth and execute.)
  10. What are we missing? What are we not considering, or who are we not considering that we should be? 

After your assistant has asked the questions above and they’ve shared their perspective on the issues at hand, it will be time to make a final decision. Assistants can use this opportunity to take their leadership to the next level by digging into your thinking and leadership style even more to learn how you think. 

They can close the loop on your decision-making with the following: 

  • I want to learn how you make decisions. Can you share more? 
  • I want to make sure I understand how you are thinking and making decisions to 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 an assistant is a process, but it’s ultimately what makes strategic partnerships work. The more trust is built (by your assistant following through and over-delivering), the more willing you will be to share how you are thinking and ask for your assistants’ strategic counsel when making decisions, especially when they come prepared with powerful questions like the ones above.

Does your assistant understand how you think and how you make decisions? What essential questions would you add to this list? Please share your thoughts below to help other team leaders and grab a few examples for yourself. 

Adam Hergenrother is the founder and CEO of Adam Hergenrother Companies, the author of The Founder & The Force Multiplier, and the host of the podcast, Business Meets Spirituality. Learn more about Adam’s holistic approach to business here.

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