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Leadership Skills Necessary for Reinventing a Company or Career

By January 7, 2014Article

Editor’s Note: “The world keeps changing, and our needs change too. So we have to reinvent ourselves,” says Craig Malloy, co-founder and CEO of Bloomfire (a knowledge-sharing, content management and social collaboration app).The need for reinventing is especially true in the disruptive software industry. But reinventing isn’t easy for a company or an individual and requires a certain mindset and skills. We featured Craig’s leadership advice in a prior SandHill article and know that he has successfully reinvented his career and several companies. So we asked him for reinventing tips. Here is his tried-and-proven advice for reinventing. 

Before we talk about reinventing a company, let’s talk about how people can reinvent themselves for a new career. This is often necessary, especially in mid-life. How can they do that, especially if they are not very visionary or entrepreneurial? 

Craig Malloy: For me it was less about the entrepreneurial part of starting a company because I had done that two times and was more about feeling like I was in a rut and wanted to do something different. It’s a little bit like my first decision to start a company back in 1996. I had been a Navy officer and had worked as an advisor to a couple of very large companies. The decision to leave and start my own company was pretty scary. I was concerned about my reputational risk. What if I fell flat on my face? 

At the end of the day it comes down to just kind of jumping off the diving board into the pool and having confidence that even if the plan doesn’t work out, you can adjust and change your plan or go do something else. Good people always have choices. They can always rebound. If you don’t take risks, then you’re never really going to learn and experience anything new. 

How bold do you have to be to reinvent yourself? It seems to me that it’s a lot more than storytelling capabilities (“I was good at doing this and here’s how that translates to this other career.”). You have to be bold because it’s a huge risk. 

Craig Malloy: Yes, but a lot of it is attitude and perseverance and just saying to yourself, “I’m going to get through this. I’m going to figure out a way to do it, even though it may be scary and a little painful.” I know that sounds corny and old fashioned, but you are what your attitude says you are. Sometimes you just have to get up every morning and go to work and make a little progress every day. I’m fortunate that I didn’t have to leave my prior successful company and start Bloomfire and didn’t have to leave the Navy and reinvent myself. I felt that I needed to leave for my own self-actualization and intellectual stimulation. 

You don’t have to be bold — you can do it incrementally. You can have a longer-term vision and goal but start biting it off in small chunks. Maybe you don’t have all the skill sets that you need and you need to take a course. A really critical first is recognizing what you don’t know, being at peace with that and being willing to sacrifice to gather the knowledge or experience that you need. Maybe you need to take a lower-paying job because that’s the field or experience that you need for your longer-term goal. When you decide to reinvent yourself or start a company, sometimes you need to take a step back to move two or three steps forward in the way that you want to go. 

I don’t think there’s any specific formula for how to do this. It’s in attitude and having a long-term goal and sticking to it. Just start, even though you don’t have all the answers. You will make progress every day. 

Does reinventing a company because of a new business model or something disruptive in the marketplace always require a top-down push? 

Craig Malloy: In the technology business every day in the news there are examples of companies that do not adapt. The ones highlighted today are the troubles of BlackBerry and Nokia, who kind of completely missed the smartphone transformation. Once you miss by not adapting quickly enough, it’s very hard to get out of that. 

Companies become enamored and a bit of a prisoner of their own success and are unwilling to make the hard decisions and uncomfortable changes or are unable to do so because of the culture that they’ve created because of the transactional friction or bureaucratic inertia. I’m sure there are people inside of BlackBerry and Nokia that saw as clear as a bell what was happening. But for some reason they were not in a position to affect the organizational change. 

At some point it does come down to the leader of the organization. Particularly in a major transformational shift like that, if the leader is not driving it, then it won’t happen. 

In times of a company’s great success, almost anybody could be the CEO. For instance, during the first four years of the iPhone, when there was no competition and Apple was crushing at every quarter, anybody could have been Apple’s CEO and would have done a fine job. But when Apple was at the depths of despair in 1991-2001, only Steve Jobs and his transformational leadership could change that company. I think in times of transformation, it does take a leader to be able to make that happen. 

What does a leader leading through reinventing or transformation need besides a vision in order to succeed like Steve Jobs? 

Craig Malloy: The CEO doesn’t necessarily have to be the greatest technology visionary; but through will and leadership skill the CEO must be able to communicate a new vision and get the organization to follow him or her to the “promised land.” The plan must be achievable. He has to lay out the steps that have to be done, painful as they may be (such as downsizing or discontinuing products) and then be able to drive the organization to accomplish those things. So there’s a very strong execution component in addition to the technical vision. 

And the CEO must pick the right team. One of my favorite examples of this is in a book called “Good to Great.” It’s the thought of having the right people on the bus and getting the wrong people off the bus. As important as it is to get the right people in the right positions, it’s even more important to get the wrong people (who either don’t have the right attitude or the right skill sets) off the bus and doing something else. That’s a critical part of reinventing. 

In Steve Jobs’ case, I think he had exceptional force of will and strong personality and great technology vision. But he also had people like Tim Cook, who was a great operations execution guy who could help implement the vision throughout the organization. Every leader is different. If they don’t have all the tools or skills that they need, they need to find somebody to fill in that piece for them. 

Whom do you personally admire as people who have reinvented themselves or reinvented companies, other than Steve Jobs? 

Craig Malloy: I think one of the great technology entrepreneurs of our time right now is Elon Musk. He decided to build a private space rocket company and start a company to build electric cars with a completely new drive chain that no one has ever seen before. He’s showing that it’s possible to transform the electric car market, and he basically put NASA out of business. 

Obviously he’s a smart guy, a good leader. I don’t know what his execution or leadership skills are, but he can certainly paint a good vision and gather a great team and get things done. Certainly from an entrepreneurial standpoint, I think he has done some amazing things and is simultaneously running two companies that are very different kinds of businesses, and it’s far afield from PayPal and what he had been doing previously in his professional career. 

And in the two companies he put his own personal wealth at risk and also put his reputation at risk. Those are very public, high-risk-of-public-failure kinds of endeavors. And he had the courage to see that through and make them successful. 

Are you now reinventing yourself again as a writer, blogger and advisor? 

Craig Malloy: A little bit. I had ideas rattling around in my head for a number of years. I’ve had some fairly decent experience in a variety of areas, and I enjoy writing. It kind of started out as complementary to our PR efforts here at Bloomfire, and I found out that I enjoy doing it. 

I feel that I have some experience that could be helpful and want to pay it forward to other entrepreneurs. If I can help somebody avoid some of the mistakes that I made along the way in my career with startups, I find satisfaction in that. 

Is there anything you tried to do over the years in reinventing yourself or a company where you failed? 

Craig Malloy: Yes. When I first got out of the Navy I wanted to go to medical school. I applied to the Navy medical school but didn’t get accepted. It was a good wake-up call. I didn’t have the right academic background or the right temperament for that. So I decided to make my career leading businesses. 

Why didn’t you try another medical school? You said earlier it’s important to keep trying. 

Craig Malloy: If I had decided to keep on that path, I’m sure I could have eventually been successful. But a part of me felt that maybe that wasn’t the right fit for me. I reevaluated whether it was what I really wanted to do or whether I was better suited to do something else. 

That’s the decision point that everybody needs to make. How far down the path do you go? Is this really something that is achievable for you, something you really want to do? 

I realized my heart wasn’t completely in that. So I decided to dig in on something else and have no regrets on that. 

You have to find something that you love to do, that you’re good at doing, and that you can make money at and build a career. Then you’re not really working. I’ve been fortunate along the way to find something that satisfies all those requirements. 

Craig Malloy is co-founder and CEO of Bloomfire. He is a Navy officer turned entrepreneur who founded ViaVideo (acquired by Polycom) and LifeSize (acquired by Logitech) and is now reinventing himself in cloud software. Building a great company out of an idea with a class-A team is his passion. Bloomfire is shaping up to be his best work yet. Follow Craig on Twitter at @craigbmalloy. 

Kathleen Goolsby is managing editor at



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