4 Questions to Ask Before Hiring a COO - David DeWolf

4 Questions to Ask Before Hiring a COO

A couple of weeks ago I was with a group of friends. We were all discussing our goals for 2015 and the bold moves that we are taking in order to ensure that we get there.

“I’m hiring a COO,” said one of my friends who runs a medium-sized business with about 150 employees.

“Is this a replacement, or a new position?” asked another, who had previously run a publicly traded organization. Based on the inflection, you could tell he was suspect about whether or not it was the right move.

It turns out that my friend was hiring into a new position in order to free himself up to focus more time on and push forward a new strategic initiative that he felt would revamp the organization. As the conversation moved forward it became abundantly clear that while he was excited about the additional capacity, he wasn’t crystal clear on what his and his new employee’s job descriptions were, how they integrated, and who would be responsible for what.

Having hired a COO under similar conditions myself, I encouraged him to ask himself a few questions.

Do you intend to allow the COO to “run the business”?

I made a major mistake when I hired a COO several years ago. My intent was to find a “running mate.” I wanted someone to assist with operations, but I intended to continue to “run the business” myself. While adding executive capacity would allow me to spend more time on the external functions of the business, I still planned to be involved.

As the “chief operating officer,” any senior executive worth their salt will likely expect to “run the business” for you. If you don’t intend to totally hand over the keys, hire a VP of Operations instead.

Do you have the right structure in place?

A warning sign that should have tipped us off to the fact that I was not necessarily looking for a COO but rather a VP of Operations was my organizational structure. The structure I created reflected my desire to run the business. Sales, Marketing, HR, Legal, and Finance all reported directly to me.

Most “chief operating” roles oversee all operations – from marketing and sales through the delivery of goods and services. While it is common for Finance, Legal, and sometimes HR to fall outside the purview of the COO, it will be nearly impossible for any executive to play a chief operating role if they are not responsible for the entire supply chain.

Do you have a plan for cascading the vision and the culture?

Adding a COO to your organization will create a level of management between you and the core of your business. This isn’t a bad thing, it’s just a reality that you need to be aware of and be deliberate about managing. As the chief executive, you are responsible for the vision, values, and culture of your organization.

“Culture eats strategy for lunch.”

“Without vision the people perish.”

No matter how strong your vision and culture currently are, adding a strong COO will likely change the way you communicate and reinforce them. Make sure that you adapt with the changes that you are making and find ways to double down even further on these key aspects of your business.

Why do you need this position now?

I have another friend who recently hired a COO to “fix” their operations. After years of under-performance, he felt as though he needed a new set of eyes. He wanted someone to come find the inefficiencies within the organization and “build a well oiled machine.”

In short, he wanted a consultant.

A strong COO has the ability to create or overhaul a strong operating model. They continually iterate, refining the business’ operating model and making it stronger while they “run the business.” They don’t just set up the model, they operate it, and it’s through the course of operations that they continually refine it.

If you’re looking for a second opinion or to just fix what is broken, you may be looking for a management consultant. Make sure you’re searching for the right thing before you hire a COO. If you’re just looking to create operating efficiencies, hiring a COO will only make your problems worse.

Deciding to hire any senior executive is something that requires serious deliberation. Hiring a COO requires significantly more. A COO can be a huge accelerator for a business, but the position’s prominence within the organization means that it comes with high risk.

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CES 2015 Recap #3: Slow and Steady - David DeWolf

CES 2015 Recap #3: Sometimes Slow and Steady Wins

If you’re looking for the latest toy, coolest gadget, or weirdest picture, go ahead and check out another blog. There are plenty of folks reporting on the sex and sizzle of the Consumer Electronics Show (CES) in Las Vegas. For me, the week was more about collecting discrete data-points and connecting the dots — boiling them down into useful insights.

In this series, I have shared trends that I think will carry forward into 2015. In Part 1, I discussed how I see the Health and Wellness industries leaping forward in 2015. In Part 2, I observed the way technology is going to engulf us. Today, I have one last observation.

One last observation: 3D Printers are now being used.

3D printing isn’t new, but it does seem to be finding its purpose – slow and steady.

Hosting a party? Don’t have enough dishes, but don’t really want to use paper plates? No problem. Just print new dishes – Martha Stewart party dishes, nonetheless.

Hardware distributor? Why carry inventory when you can create low volume parts on-demand?

Hardware R&D? Rapidly iterate through various experimentations. Tweak a model and reprint.

I’m not sure exactly where 3D printing is going to end up, many of the use cases do seem to still be immature, but, it’s becoming more and more popular, more and more refined and is slowly entering into mainstream.

Oh, and printer prices are starting to come down to the point where they are affordable by the average person. That will prompt further innovation and adoption.

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Fatal Flaws in Business Relationships - David DeWolf

What to Do with Fatal Flaws in Business Relationships

Have you ever had that really, really difficult client? The one where you love their business model, you love what it is they do, and in fact you even love the executives and owners of the company and believe that they’re good people?

Certain people have character traits that make it difficult to work with them in business relationships (and life, too!). I have a client who has a fabulous idea for building a product. They have been successful in obtaining clients and the gentleman I’m working with is a multi-time entrepreneur. He has capital and access to capital.

But, unfortunately, he lacks follow through. We can have a discussion and make a commitment, and that discussion will not come to conclusion or be followed up on within six months, despite constant reminders.

This makes it horribly difficult to manage the relationship and even makes the relationship a little bit shaky sometimes. It’s a difficult situation to overcome.

I have found that the best way to manage these types of relationships with these flaws is very directly and bluntly. Despite having great relationship and a great respect for this individual, it’s important that I give blunt feedback. I’m very direct with what this means for the relationship.

The hardest relationships to navigate in business are the relationships that have so much potential and have such a strong foundation, but there’s a crack in the foundation that jeopardizes the structure. Those cracks can be fatal. Despite all the other wonderful characteristics can really get in the way.

This goes for employees as well. With employees, the same thing can be true. You can have someone who is absolutely phenomenal in certain areas: they have all sorts of talent and maybe they’re a great culture fit. Perhaps, though, they don’t follow through on their commitments.

This can send waves throughout the organization if you boost them up as leaders, as they so often seem to be, because others around them can raise questions: Isn’t it important that we follow through? Isn’t it important that we’re timely in our responses?

It’s a difficult situation. Those relationships that are the most difficult to terminate are not those that are totally off. It’s also not those that you don’t need to. The ones that are so difficult to manage are the ones that are so close, yet have that fatal flaw.

What should you do in those situations? Be blunt, be deliberate, and call it out. If the behavior doesn’t change, cut them off. They have become greater distractions than they need to be.

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You Don't Have to Agree to Respect and Support - David DeWolf

Why You Don’t Have to Agree to Respect and Support Someone Else

It took Teresa and I a while to get on the same page about homeschooling our kids.

Homeschooling is something that she’s very passionate about and deeply committed to. She enjoys creating a home full of learning experiences, spending time with the kids, and educating them during their most formative years. From the earliest days of our marriage, she’s been committed to homeschooling our children.

I, on the other hand, was skeptical at first. It took me a while to fully embrace our homeschool decision. Frankly, while I supported it early on, it was with great hesitation. Over time, I have been able to see the many benefits that it has brought to our family.

Over the years, especially in those early years of skepticism, I have had to continually remind Teresa that while I didn’t fully agree with the decision we made together, I did fully support it.

Too often we confuse support with agreement. You and I can support decisions that we don’t wholeheartedly agree with. It requires a greater purpose. It requires a commitment to a team, or an overarching objective, that supersedes the decision itself.

In business, we call this alignment. Fully aligned teams trust their leader to have the overarching objective and good of the team in mind. After engaging in healthy debate, a decision is made and the team moves forward, fully committed.

Respect is similar. I can respect your opinion without agreeing with it.

Someone that I’ve been very close to for years has been adamant lately that I don’t respect him. He’s confusing the fact that I disagree with him about a few, albeit very important, topics, to mean that I don’t respect him. Nothing could be further from the truth. I respect him and I respect the decision he has made for his own life (it’s not a matter of ethics or morals, just a philosophical difference on how he wants to live his life).

Unfortunately, this friend wants me to agree with him. He wants me to affirm that I would make the same decisions and to tell him that he’s “right.”

In some things in life, there is no “right” or “wrong.” There’s just different.

There’s more than one play that a coach can call when a winning shot is needed. There’s more than one way to school your children. There’s more than one way to market your services.

Don’t confuse moral from amoral decisions. Don’t confuse support and respect for agreement.

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The Weekly Shufflepass - David DeWolf

The Weekly Shufflepass Episode #005: Checking Out to Accelerate Marriage and Work [Podcast]

The Weekly Shufflepass is a series of short podcasts in which I talk about something that’s on my mind. They are quick tidbits. No frills. No production. Just helpful thoughts on how you can go, do something greater than yourself.


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As Type-A personalities, we rarely give ourselves a break and focus on non-work areas of our lives. In this week’s Shufflepass, I share how I was able to check out of work for my 15th anniversary trip and in doing so accelerate marriage and work.

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A Lesson in the Integrated Life - David DeWolf

How My First Business Trip Taught Me about the Integrated Life

Living the integrated life isn’t always easy. I’ll never forget the first business trip I ever took.

I was fresh out of school and fresh out of living quite a protected life. My first job was as a consultant. Within a couple of weeks of starting, I was on the road headed to San Francisco to do consulting work.

On the first night of the trip, a group of us headed out to dinner. Being naive, I had no idea what was about to happen. I’ll never forget when I realized on the way to the restaurant that these men were intending to go to a strip club for dinner.

Needless to say, as an engaged Catholic man who believed that that was not the right way to live, I jumped out of the taxi and headed back to the hotel, trying to figure out what to do for dinner and how to handle the situation.

It was quite awkward, and it was a situation I wasn’t prepared for.

This is what set me on the path of motivating myself to make sure I had strong relationships with others to support me and hold me up. This set me on the path for being intentional about living an integrated life.

Just because you’re on the road and away from your family doesn’t mean you’re not a husband or father. Just because you’re at work doesn’t mean that you’re not a dad. Just because you’re at home with your family doesn’t mean you don’t have responsibilities at work.

What I’ve found over and over in my career is that there’s this mentality that we have to balance our work and our life, that they are somehow in conflict and that, to put them in proper balance, we have to bifurcate ourselves.

I’ve found that living a healthy life means integrating all aspects of my life. I’m a much better husband when I remember that I’m a husband all the time. I’m a much better professional when my job is in my mind all the time. I’m a much better husband and father when being a parent is on the top of my mind all the time.

Sure, there are points in time when I need to focus on the task at hand, but I don’t chop one part of myself off simply because I have a task to do in another area of my life.

I am who I am. I’m a husband when I’m traveling. I’m a father when I’m at work. I’m a CEO when I’m at a kid’s activity.

Living the integrated life is what makes healthy individuals. It’s what makes us live up to who we are called to be.

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