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Writer's pictureDerek Ling

3 Questions That Help You Evaluate a Great (or Not-So-Great) Leader

Updated: Oct 23

I work with clients from across tech and Fortune 500 companies, and it’s interesting to see the challenges that impact leaders across the diversity of industries from SaaS to Pharma, and Directors to the C-Suite.


One common challenge I hear from my clients is, “How do I evaluate whether or not I’ll thrive working for a leader during the interview process?”

 

To help answer that question, one of the exercises that I have my clients perform is to reflect on leaders they have worked well with in the past.

 

I ask them to write down their character traits and management systems they learned from those leaders, how it impacted them, and what they have adopted as part of their own leadership system.

 

This helps people identify and define two things:


  1. Their own definition of leadership and the environment that they create for their team.


  2. The type of leader that they will more likely succeed under in the future.


We perform this self-reflective exercise before clients start interviewing for external roles so they have an evaluation criteria to evaluate a potential leader.


How to Evaluate a Leader

 

If you’re actively interviewing for a new role, here are three questions that are vital to ask your interviewer:


  • How are the company values and leadership principles incentivized as part of the reward system?


  • How do you approach developing talent?


  • What has been your track record of producing other great leaders?

 

❌ If they say “we don’t have a system set up yet” (common for startups), make generalized statements without giving examples, or you’ll be working for first-time manager, those are all red flags.

 

✅ So what is a green flag or a good answer?

 

Something along the lines of:


  • “These are my leadership principles…”


  • “Great performance is rewarded on my team in a variety of ways including verbal recognition at team meetings and 1:1’s, compensation awards, and promotions.”


  • While we have a recognition-driven culture, we balance positive recognition with constructive feedback. Constructive feedback isn’t provided at annual performance reviews, but when we see there’s an opportunity for improvement.


  • “One of the main reasons why people join my teams and continue to work for me is that I have a track record of developing other great leaders. These people have gone on to be marketing leaders at other companies,” etc.



A chess board
In an interview, you're evaluating your potential future leader just as much as they're evaluating you. Make sure to ask them the important questions as well.


Introducing Bill Walsh and the Concept of the Coaching Tree

 

For those of you who aren’t football fans or the San Francisco 49ers, you’ve likely never heard of Bill Walsh. He was the coach of the 49ers for 10 years and led them to 3 Super Bowls.

 

Bill Walsh's influence on the NFL extends far beyond his legendary success as head coach of the San Francisco 49ers. Widely regarded as one of the greatest minds in football history, Walsh’s real genius may lie in the people he developed—his coaching tree, those leaders that were produced as a result of learning from him, is one of the most expansive and successful in the sport.

 

While Bill Walsh retired from coaching in 1989, his impact on the game is still felt today at the highest levels. Andy Reid, the coach of the Kansas City Chiefs, Kyle Shanahan, the coach of the SF 49ers, John Harbaugh, are a few of the 31 NFL coaches who are a part of his lineage.

 

Investigate the Track Record of the Hiring Manager’s Ability to Produce Other Great Leaders

 

Taking the coaching tree concept into practical application in the corporate world, while asking questions of the interview team and hiring manager are a critical part of the evaluation process, analyzing their real life results will help you separate truth from fiction. After all, any great recruiter and interview team will “sell” you on exactly what you want to hear.

 

Perform a search on LinkedIn and analyze the interview team and hiring manager. Evaluate where they’ve worked in the past, reflect on what those cultures were known for, and how much progress the team has had underneath that manager.

 

If everyone has been stagnant for years, there’s either a problem with the environment or a problem with that leader. 

 

On the other hand, if the team seems to be getting regular promotions, working their way up the ladder, and growing their careers at a company that’s known for producing great products, this is a good sign. 

 

While many people tend to go with their gut and stray away from asking the tough questions, I’d recommend a contrarian approach… that you do your research and ask the important questions.

 

This can make all the difference between setting yourself up for success or ending up working for a leader that adversely impacts your career and the quality of life.

 

Grab your Spot in my Executive Branding Suite

 

I’ve been signing new clients every week to my executive branding suite. I work with clients to:


  • Unearth their why


  • Uncover how they’ve led through adversity


  • Develop case studies of transformative work that they’ve done for businesses they’ve worked with and how they’ve solved problems using AI and ML


  • Develop mastery with storytelling and navigating the interview process


All of this work is preparing them for all the questions they’ll get in their interview.

 

This is a game changer. We’re teaching them how to speak about themselves in a way that’s 10X what they’re currently doing.

 

We’re working with PhD scientists who are now leaders, sales leaders in the ad tech industry, and many others. There’s no shame in getting a coach – if Michael Jordan needed a coach, maybe you do too. 😉

 

If you’re looking for a company that can simplify the self-discovery process, increase your leads, and success rate in the job search process, don’t hesitate to reach out.

 

 

Stay Connected

 

If you’re looking for support navigating your career, I’m here to help.

 

 

“To be yourself in a world that is constantly trying to make you something else is the greatest accomplishment.”

– Ralph Waldo Emerson

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