20 Questions Leaders Should Ask Themselves

Share on Facebook
Share on Twitter
Share on LinkedIn
ADVISA CEO, Heather Haas celebrates 20 years

I recently celebrated a career milestone that sounds wild just saying it: It’s my 20-year anniversary at ADVISA. And while it surprises me to say that it’s been 20 years, it doesn’t surprise me that I’m still here. This is a team unlike any other, and it has been my honor and privilege to grow along with it.

You see and learn a lot in 20 years. I can’t count the number of times I have watched our team transform work cultures into places where people love to be – or how many leaders we’ve helped grow into the best version of themselves. It’s beautiful to witness those transformations unfold.

At ADVISA, we like to say that transformation is a journey not an event. Every journey is quite different, but many of the underpinnings of success are the same. You have to challenge your team, but you also have to challenge yourself as a leader. And you have to regularly seek out new perspectives.

In my experience, the best leaders never stop learning and they challenge themselves, at least in some small way, almost every day. In the spirit of my 20-year anniversary with ADVISA, here are 20 questions leaders can use to challenge themselves and keep growing.

20 questions:

1. What values inform my decisions, and am I staying true to them?

Living in a values-aligned way is the oxygen of fulfillment. 

2. What kind of leader does my team need me to be today? 

You can’t meet others where they are if you’re not seeing them and listening. To lead the people is to lead the company.   

3. Am I cultivating the type of work environment that supports growth? 

As part of my masters, I read the book The Fifth Discipline by Peter Senge and have carried the power of systems thinking into my leadership.  His approach to growth was not to push it but rather to remove the factors limiting growth. This small pivot in thinking has led to important decisions and investments.

4. What needs to be communicated today? 

Where I have made missteps over the years, it’s largely been a failure to communicate. Most leaders dramatically underestimate how often and how much they need to communicate important things.

5. How are the other members of my leadership team doing? 

The senior leadership team is the marrow of any organization. It’s also the key to “letting go of the vine” as the CEO. It’s impossible to step aside and let your leadership team soar if they aren’t capable, healthy (mentally, physically, spiritually) and if they don’t enjoy and trust one another. 

6. What motivates me, and how can I use it to inspire others?

I love to learn and share. When I can share perspective, ideas, insights and interesting information with others, it’s a very authentic way for me to connect and it reveals a bit more of who I am to my team.

7. Who have I not heard from and/or seen lately?

We are an office-first culture so when people aren’t coming around, it’s a concern and it’s a flag to reach out to them. Belonging is one of our core values and it requires intentionality.

8. What do people not know that they should know about the performance of the business? 

Fostering a culture of openness and transparency is very important to trust and decision-making. When people know the score, they understand why we call the plays we do.

9. Who needs recognition and encouragement?

When I was a teacher, I had a wonderful assistant principal who would write handwritten notes of encouragement and leave them in teachers’ mailboxes and send them home to students. He said that the power of giving someone a specific and genuine compliment cannot be underestimated. I agree.   

10. What is giving me energy right now and what (or who) are my energy vampires? 

I’ve learned that managing my energy is key to my productivity and best thinking.

11. Do I encourage experimentation while minimizing fear of failure?

When things go wrong, I try to seek first to understand, empathize when necessary, and then go forward better than we were yesterday. 

12. Am I building resilience and adaptability within my team?

Our founder, Bob Wilson, taught us that confidence is the currency of productivity. And, confidence is forged through adversity by doing the hard things. Letting team members wrestle with their problems and offer recommendations (versus solving the problem for them) is very important to developing their core confidence.  

13. What am I grateful for?

Whenever I feel overwhelmed, stressed or frustrated, I stop and write a few thank-you notes. It’s a very important way to flip my mental script.

14. Am I learning from and leveraging what our newest leaders are doing?

One of the greatest joys of promoting new folks into leadership roles is seeing the organization through their eyes and learning from how they do things differently.

15. What am I doing to give my team a sense of purpose?

Everyone deserves to have “line of sight” between what they do every day and the broader aims and aspirations of the company. Purpose inspires and connects us.

16. Do I promote and personally demonstrate work-life balance?

This is a tough one because leading a small business is hard and stressful. Being honest about times when I’m not prioritizing my own wellness and asking for support is something I try to model so that others feel safe doing the same.

17. Am I providing my team ample opportunities to learn and grow?

Most of the professional development at ADVISA during my 20 years has come from stretch assignments, coaching and employees attending our own programs. I think in the next 20 years (well, likely 10 for me 😊) it will be important to offer more external opportunities for people to learn and grow as well as clarity around career pathing.

18. Am I fostering a culture of continuous learning and improvement?

We believe you haven’t learned if you haven’t changed. So, we routinely surface “do differents” and improve processes to minimize mistakes. 

19. What does the future hold?

As CEO, I believe I am chiefly responsible for casting a vision for the future and bringing that vision into focus for the organization. I love imagining what’s possible and trying to see around corners.

20. What legacy do I want to leave as a leader?

Legacy comes from the Latin verb, legare “to appoint by a last will, send as an ambassador.” I hope my legacy is a lineage of caring and effective leaders who will be ambassadors for positive change in the world — the ones I have personally selected, coached and developed at ADVISA, as well as the leaders we have impacted through our learning experiences and tools.    

That may sound like a lot of questions, but…

It’s really just the tip of the iceberg.

Leadership is complex, and there is no one-size-fits-all path to success. But there IS a process we know works.

Regardless of what your organization’s biggest leadership challenges may be, my experience shows that transforming your work culture can change everything. And, coincidentally, the biggest driver of culture is your leaders. It’s two sides of the same coin.

Helping organizations transform their culture is my passion. It’s exciting, and I love to talk about it. Want to know more? I’d be happy to speak at your next event. Just say the word, and I’ll be there.

Cheers to 20 years.

Cheers to the power of transformation.

Cheers to all the leaders — we’re in it together!


Here’s another leader’s perspective on how much can change in 12 years when you’re focused on helping companies build cultures where people love to work.