New Leader Checklist: 4 Questions to Ask if You Want to Lead Effectively

Guest Post by Ken Downer

Whether it’s your first leadership position or your fifty-first, taking over can be a challenging business.  One key to success? Don’t start out by answering questions; start by asking them.  Today we’ll talk about four new leader questions you should ask, and how to get the answers so that you can lead confidently and effectively.

Have You Heard This One?

A company, feeling it was time for a shake-up, hires a new CEO. This new boss is determined to rid the company of all slackers. On a tour of the facilities, the CEO notices a guy leaning on a wall. The room is full of workers and he thinks this is his chance to show everyone he means business!

The CEO walks up to the guy and asks, “And how much money do you make a week?” Undaunted, the young fellow looks at him and replies, “I make $600 a week. Why?” The CEO then hands the guy $600 in cash and screams, “Here’s a week’s pay, now GET OUT and don’t come back!”

Feeling pretty good about his first firing, the CEO looks around the room and asks, “Does anyone want to tell me what that slacker did here?” With a sheepish grin, one of the other workers mutters, “He’s the pizza delivery guy.”

(Credit to Rare Leadership Solutions)

First Impressions

A successful start as a new leader doesn’t require bold actions or drastic measures.  And if you try to start leading before you know what’s going on, you risk firing the pizza guy and looking foolish, like our CEO in the joke above.

A strong foundation for effective leadership is built not on dramatic acts but on understanding the environment, and building trust, so that when it is time to take action, your team will be willing to follow you.

Effective leadership is based on understanding the environment and building trust.

To establish those things, here are four questions you should ask, why they are important, and some tips for how you can get the answers you need.

4 Questions


 1. Ask:  What is the vision?

This is all about knowing the direction you need to take the team.  Leadership is influencing others to get something done, so it’s crucial to understand what the long term vision of your organization is, and the short term goals you need to meet to get there.

Get the answer:  The best way to get this is to meet with your boss.  Even if you already know the organization and each other, do this anyway.  It’s important to sit down and discuss their specific expectations.

It can be intimidating if your boss doesn’t initiate a meeting, or seems too busy.  But set it up and make it happen.  You can’t lead effectively if you are uncertain about the direction you are going.

Helpful tip: Take a checklist into the meeting with you to help make sure you ask the right questions.  Here’s a free downloadable interview checklist that you might find helpful.

2. Ask:  What are the team’s strengths and weaknesses?

This is all about who’s on your team and what they can do.  Maybe you have been around a while and already kind of know.  Or you are the newest kid on the block and don’t know anyone.

Either way, it’s worth the time and effort to deliberately evaluate the relative strengths of your team members and compare that to what your team is supposed to be doing.

Get the answers:  Talk to each member of your team.  Get to know them as people, and ask them to explain what they do, how they do it, and what challenges they face.

By developing an understanding of who is on your team and what they can (and can’t) do, you are laying the foundations of trust and improving your grasp of team capabilities.

When you know what obstacles are holding them back, you will be able to see how you can help clear the way forward.

3. Ask:  What don’t you know that you should?

This is about your personal competence in your leadership position.  It’s directly related to building the trust that is so essential on an effective team.

An early mistake new leaders can make is to try to act as if they already know everything.  Even if you think you do, people will shut down on you if you act as though no one can teach you anything.

Get the answers:  The best leaders I’ve known were always full of questions and curiosity, even when they thought they knew the answers.  They were confident, but when they didn’t understand something, they wouldn’t try to hide it.  Instead, they became intensely curious.

They would ask lots of open-ended questions like, “tell me more about how that works,” “how do you fix it when it breaks” and “where do you get the resources you need?”

And when you identify an area of knowledge that you can’t fill in a short conversation, make a plan to get smart.

Who would you rather follow – someone who pretends to know everything or the person who admits he doesn’t but actively strives to fill in a knowledge gap whenever he finds one?

4. Ask:  Who do you need to know?

As the leader, a crucial part of your job is synchronizing the actions and efforts of your team with the rest of the world.  To do this you have to have a leadership network.

Get the answers:  Think about who your team supports or gets support from on a regular basis – it could range from suppliers to maintainers, marketers, customers, finance, and human resources.    Also ask your boss who you should get to know.

Make a list, then go introduce yourself.  Do it before you need something from them.  Ask about what they do, how they interact with your team and about any challenges they are having that have involve your team.

Build your network of key contacts before you need something from them.

Simply connecting with people and showing that you are interested in them will open doors, improve your understanding of your environment, and give you places to turn when problems arise.

New Leader Questions – The Takeaway

Being a new leader can be tough even under the best of circumstances. One of the best things you can do to make it easier on yourself is to get clear on the direction, fill in your knowledge gaps, and get connected to others who can help you move your team forward.

This list just scratches the surface of how to focus your efforts in the early days of a leadership position.

If you are interested in learning more about how to approach your new leadership position, consider checking out the Essential Leadership Skills for the New Manager Course.

The course is loaded with short videos, helpful tips and techniques, and a bunch of guide sheets you can use to stay on track.  It’s all designed to help you ask smart questions and take the right actions to help you excel in the early days of your new leadership position.

After all, firing the pizza guy is probably not the way you want to start things out…

Lead on!

Ken Downer


Ken Downer has been a leader in many capacities, from his 26 years in the Army to his 17 years in the Scouting program.  His passion is sharing what he has learned about leadership with other leaders, particularly the next generation.  You can connect with Ken on Twitter or LinkedIn or catch his weekly leadership insights at his web site,


One Engaging Question

Excerpted with permission from Chapter 5 of “The Power of Conscious Connection” by Talia Fox Pam was...

“MY GOD, MY GOD, WHY HAST THOU FORSAKEN ME?” Questioning with Jesus Who Questions with Us

By Matthew Lee Anderson – Excerpted from the 8th Chapter of “340 Questions Jesus Asked”...

10 Questions to Ask Your Dad (or Grandpa) on Father’s Day

My Dad, Arnett Tiede, was the greatest influence on my life and was always my "Hero!"...

If You Ask Me

Note From Bob:   How many times have you connected with someone who has lost their spouse and not quite...

Do you know how to lead with questions?

Originally posted @ Many leaders find themselves working with teams from diverse backgrounds....

A Simple Recipe for When Conversation Feels Stuck

Guest Post by Amber Johnson A few years ago, I heard a cookbook author on a radio program. She mentioned that...

Everyone Can Ask Powerful Questions

Excerpted with permission from the 20th Chapter of “When Everyone Leads” by Ed O’Malley and...

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.