Tag Archives: questions

How can you help your team crush 2016?

Wood arrow sign with 2016 loading handwritten on old page of paper nailed to planks, green grass around, isolated on a white background.A former client (and now friend) asked me to speak to his team this past week. He’s a great guy, caring leader, and a hard working executive who is always interested in growing and learning.

His business has been hit with unrelenting head winds and his team has had some recent attrition. But, rather than give up or tread water in place, he wants to help his team find inspiration and motivation to not only get through this rough patch in 2016, but also excel and write a new story this year.

He wanted me to share some ideas that would help his team’s mindset and encourage them take action to rock 2016.

Here’s what I shared with them.

1. ATTITUDE #1 – It starts with you:

We started with a fun exercise. I asked them all to take one blue sticky note from the pack that I gave them. Then, I asked them to place the sticky note as high as they can on a wall in the room.

When they were all settled back in their chairs, I asked them to retrieve their blue sticky note and place it higher than where they initially placed it. Some climbed tables and chairs to place it higher and some stuck it to the actual ceiling. One person, my former client, left the room, rode the elevator to a higher floor, and placed it on the wall there. 

My question to them was, “Why didn’t you do that the first time?” As leaders, our own limiting beliefs not only impact our own performance, but our team members’ performance as well.

Point: Your attitude is everything. Question your limiting beliefs.

Question: Does your team’s performance in 2016 start with your own attitude?

2. ATTITUDE #2 – Embrace the constraints:

There are a lot of constraints on building a successful business. Money, time, family commitments, education, taxes, local infrastructure, etc. The list is endless. But, what if constraints actually helped, rather than hindered.

There is a fair amount of research that suggests constraints can actually be used to increase motivation, performance, and success. One of the classic examples is the story in the book, The Goal, by Eliyahu M. Goldratt. Using the Theory of Constraints in manufacturing, the main character is able to turn around an underperforming business by embracing the constraints.

But, the example I used during my time with this team was the story of Futsal. James Clear does a nice job of outlining the history of this soccer-like game that was developed in 1930 in his article, “How Constraints Make You Better: Why the Right Limitations Boost Performance.” When students played Futsal on a small surface area, with fewer players, and with a smaller ball, it actually increased their ability to play soccer. Read the article and you’ll see why “constraints” and Futsal helped Brazil win three World Cups.

In my own work with Founding CEOs I’ve seen the same idea applied nicely. “Since we didn’t get the full amount we expected in this seed round, how can we still meet our objectives?” It’s a powerful question that taps into the deep recesses of our imagination in a way that an abundance of resources just can’t do.

Point: You can actually use constraints to improve performance. Embrace them.

Question: Are you tapping into the power of constraints?

3. ACTION – Ask more beautiful questions to encourage greater creativity:

I have a lot of favorite books. It’s a problem. 🙂 One of them is “A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas,” by Warren Berger. He does a nice job of helping all of us understand the power of questions to help individuals and teams really break through.

When I spoke about this topic to last week’s team, they did like most do when I bring up this subject. They think it’s a great idea and then want me to provide examples. I shared a few and then engaged their brains to think of some. In my opinion, it’s not about more effective questions, it’s about more beautiful questions, just like Warren’s title. It’s the type of question that taps into your team’s imagination.

Here’s one you might chew on for awhile: “If 2016 was our last year in business, what achievement bullet would you want to be top on your resume to help you get an even better job in 2017?” Can you see the underlying power behind this question?

Point: You can serve as a catalyst to your team’s fatalistic thinking and flip it around to make great things happen in 2016.

Question: Are you asking more beautiful questions?

4. NATURAL INFLUENCE – Know, Connect, & Leverage Your Team’s Motivations:

By this time, the team I was with was just starting to warm up to me. But, they were still skeptical.

The common mantra at this organization is, “We need to drive performance.” I can’t tell you how much I loathe that statement. It comes from an attitude that suggests pushing is best. It suggests that it is our energy as a leader that is needed to get performance from our team members. I’m sorry, in my experience, it just doesn’t work that way.

How does it work? Tap into the individual and collective motivations of your team members and that is how you and your team will crush 2016.

What does that look like in practice? Well, here is a question that one of the participants asked me: “What do we do with our low performers?” It’s a common and legitimate question. But, my response is the same. Tap into their individual and the collective motivations of the team.

Each member of your team has a set of interests that energize them, a set of expectations about how the people and the environment interact with them, and a set of values that currently inspire them. It’s your job as a Founding CEO to help your team members gain clarity on these motivators and help them find a connection to the goals of the organization. How? Coaching conversations that focus on them, rather than on you, often work.

So, what about the collective motivators? Dan Pink’s book, “Drive: The Surprising Truth About What Motivates Us,” is a great primer on this subject. His and others’ research suggest that autonomy, mastery, and purpose are three key common motivators amongst all of us.

  • Do you team members feel in control?
  • Do your team members feel like they can use their full potential and grow?
  • Do your team members feel like the work your company does matters and is making a positive impact?

I told the group a story of a rather embarrassing incident when I was a young platoon leader in the Army. I thought my soldiers needed a morale boost so I went out and found an artist to create what amounts to a team logo on a flag stick. In the military we call it a guidon. Well, it was a disaster. They hated the design, hated the idea, and it did the opposite of what I intended. Why? It was not their idea. They weren’t in control. It didn’t help them grow or learn in any way. And, it certainly didn’t matter or make a difference on our mission.

I learned an important lesson.

Point: You can help your team find their individual and collective well spring of motivation in 2016.

Question: Are you helping to tie your team’s personal and collective motivations to the mission?

In summary

Attitudes, questions, and motivators. Get these things right in 2016, and you and your team will crush your objectives this year.

What do you think?

What will you do differently in 2016?

Send me an email and let me know.

Boost your leadership, fast? Read these 6 Books!

Screen Shot 2016-01-10 at 10.08.16 PMHarry S. Truman is quoted as saying, “Not all readers are leaders, but all leaders are

I agree.

Accelerating the learning that is required to transition from Founder to CEO is pretty important. I have personally found that regular reading has helped me.

When I was an officer in the Army, I did not spend the time I should have. I didn’t read as I should have. Because of that, I’m sure my own personal leadership development didn’t progress as fast as it could.

So, when I became a Founding CEO myself, I decided to change that. I started to read, read, and read. Now, it is not unusual for me to read 3-5 books a week. Not all of them are 300 page tomes, but they are books indeed.

I would like to help you. I’ve collected what I think are 6 books that can help jump start your leadership, fast! Think of this as your 2016 reading list…for the first six months…one per month.

1 – Big Impact

Title: Hot Seat: The Startup CEO Guidebook

Author: Dan Shapiro

Description: Shapiro mixes first-hand Startup CEO experiences with the experiences of other Startup CEOs he has interviewed. He created a masterfully crafted and very practical book that every Startup CEO should read. He covers almost all the topics you would want insights on: decision-making, delegation, raising money, and more.

Why you should read this book: I like it because it is an easy read and very practical. You won’t find fluff or bloviating or puffed up personal drama. It’s a straight forward book that packs a lot of learning. I recommend it to everyone.

2 – Tough Love

Title: The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers

Author: Ben Horowitz

Description: Horowitz is well known as one of the leaders of VC firm Andreessen Horowitz. He chronicles his leadership lessons from the many high profile companies he led. MANY of the Founding CEOs that I have interviewed have read the book. The reason? It’s an unvarnished, in-your-face account of entrepreneurial leadership that really makes you question whether or not you should take the leap. It’s that good.

Why you should read this book: If you want an account of what struggle looks like, you should read this book. Ben seems to have experienced almost everything a Startup CEO can experience. But, it’s his personal feelings about the ups and downs and the practical advice he shares that makes this book a must read.

3 – Key Decisions

Title: The Founder’s Dilemmas: Anticipating and Avoiding the Pitfalls That Can Sink a Startup

Author: Noam Wasserman

Description: This research based book captures many of the common dilemmas that Founding CEOs encounter as their journey to CEO. Noam Wasserman reveals these common pitfalls and decision points in a way that is easy to read and relatable in many ways.

Why you should read this book: I like Noam’s book because he has condensed his research into a practical flow chart of issues that most Founding CEOs face. You can literally keep it on your book shelf and refer to it every other month and find your next dilemma and advice on how to navigate the dilemma. Several of my coaching clients have read it and attest to its profound impact on their lives – most through better, more informed decisions.

4 – Great Reference Guide

Title: Startup CEO: A Field Guide to Scaling Up Your Business

Author: Matt Blumberg

Description: Blumberg has created one of the most detailed reference guides on Founding CEO leadership on the market. He covers more topics than any of the other books. He offers valuable insights into how the CEO sets the overall vision and strategy of the company and communicates it to all stakeholders. He discusses how to build a company’s human capital by recruiting, hiring, and retaining the very best talent. He examines how a CEO must align available resources with the company’s strategy in order to ensure success. And, there is a lot more than these topics.

Why you should read this book: This is not necessarily the type of book that you read cover to cover in one sitting. It is rich, dense, and packed full of very specific tips on an array of topics.

5 – Processes

Title: Startup Leadership: How Savvy Entrepreneurs Turn Their Ideas Into Successful Enterprises

Author: Derek Lidow

Description: Lidow’s experience as a Startup CEO and his time as a Princeton University professor combine to create a wonderful resource. The best part of the book are the actions he believes you should take at the key developmental phases of your business. It’s heavy on processes and light on sentiment. But, he clearly delineates what you need to do as a leader during each phase your business goes through. I think this aspect of the book is very insightful and helpful.

Why you should read this book: If you have no idea how you should be spending your time, this is a great book for you as a Founding CEO. Derek breaks it down very clearly and I believe makes a great case for understanding the processes inherent in Startup CEO leadership.

6 – Unique Angles

Title: The CEO Tightrope: How to Master the Balancing Act of a Successful CEO

Author: Joel Trammel

Description: Joel has an amazing track record of success as a Founding CEO. His analogy of a tightrope that a CEO must balance on is a great image to keep in mind. He covers many topics and angles that are not often covered. For example, I like his chapters on decision making and how it relates to building consensus.

Why you should read this book: It’s a well written book with some unique angles on Founding CEO leadership that you will appreciate. I also think his style of writing is well suited for a weekend read or a flight across the country.

Send me an email when you are done.

What’s your biggest insight?

What questions do you ask your team?

Woman asking questions to sales managerWhen people ask me what I do as an executive coach, I often say, “I ask questions.” Yes, I get paid to ask questions. Often times the CEOs I work with struggle to answer the questions I present to them. That’s good. It’s a starting point for learning, growth, and development.

The same is true for you and your leadership team. Do you ask them questions?

Over the past six months I have been working on a leadership development guide for Founding CEOs. It is intended to help you become a great CEO. What’s one of the top skills I suggest all Founding CEOs work on? Asking better, more effective questions.

Asking questions serves you, your team, and your company in many ways. But, I won’t go into them in this blog entry. It’s the start of a new year and I would rather help seed your thoughts with questions that your fellow Founding CEOs ask their teams.

I try to ask CEO guests on the “From Founder To CEO” podcast about their best questions.

The question I ask them is: “What is one of your favorite CEO questions that gets powerful results from your team?”

I’ve compiled their questions for you. You might want to try some of these in 2016. They are good!


  • “How do we take this thing and make it exceptional?”  (Joshua Dorkin)

Moving Things Forward:

  • “If you could only do one of these things, what would you do?” (Tope Awotona)
  • “Is there anything getting in your way right now?” (Caitlin MaGregor)
  • “Is there a bottleneck?” (Caitlin MaGregor)
  • “What is the one thing that you need to get done today?” (Joshua Dorkin)
  • “Are you focused on the right things today, to produce the things that need to be produced?”  (Joshua Dorkin)
  • “What are the three big take-aways from our meeting?” (Joel Heath)

Being Supportive:

  • “Is there something we can do to make your life better and what would that be?” (Caitlin MaGregor)
  • “Is there something you are struggling with?” (Caitlin MaGregor)
  • “What is the one thing you are thinking about today?”  (Joshua Dorkin)
  • “How are things going?” [Do it in a certain scenario…pick the time and situation where they can really open up to you.] (Andrew Krebs-Smith)
  • “What is your Rose?” [The thing that is going really well or that you are most proud of.] “What is your Bud?” [The thing that is on the horizon that you are most excited about.] “What is your Thorn? [The thing most frustrating you.] (Mattan Griffel)
  • “What are the struggles that you are going through, and how can we get around them?” (Joshua Dorkin)

Encouraging Problem Solving:

  • “What do you think of the results yourself?” (Steinar Henskes)
  • “How would you make this decision if you were the CEO?” (John Bodrozic)
  • “If there is a resource constraint or time constraint, what would you do, and why?” (Tope Awotona)

Probing Further:

  • “What’s the one thing I didn’t ask you that you are glad I didn’t ask?” (Bryan Miles)

Goals & Priorities:

Do you have questions that serve you well?

What do you you ask your leadership team?

Share them below so we can all benefit from them.

Happy New Year!