The cybernetic startup & why delegation is a key skill of successful leaders


I started my professional career in the sound reinforcement business as an individual contributor working first for Bill Hanley, of Woodstock fame, and later for his brother Terry, who was doing the sound for Aerosmith at the time I started working for him. Before that I’d been helping my friend Nancy Talbott of the Boston Area Friends of Bluegrass and Old-time Country Music by recording the concerts she put on and eventually doing the sound reinforcement for music greats like Bill Monroe and Doc Watson. Through my connection with Nancy I ended up working as the chief sound reinforcement engineer at The Performance Center in Cambridge. But there I was thrown into management without any idea of what I was getting into, as The Performance Center had two music rooms, each running seven days a week. There was no way I could handle that myself so I hired two friends of mine to fill out the schedule. But my management responsibilities consisted of simply scheduling everyone and ensuring we had backup in case one of us got sick. I hardly thought of myself as a manager and frankly no one else did either! The word “delegate” wasn’t even in my vocabulary.

I still thought of myself as an individual contributor when I changed careers after getting my M.S. in Library and Information Science. However, my first and only manager as a community librarian/media specialist was a great leader – Sigrid Reddy knew how to get more done with less resources, the mark of a successful entrepreneur, despite being an employee of the Town of Watertown. So thanks to her I ended up managing several professionals we were able to hire through government grants: two photographers, a graphic designer, and a filmmaker. As their manager I saw my role as simply getting them the resources they needed to do their jobs and collaborating with them on the direction of their projects. The word “delegate” stayed dormant in my vocabulary.

I had to learn how to delegate and  learn fast when I was thrown into the deep waters of a successful software startup. Although the leaders of Software Arts – the inventors of VisiCalc, the first electronic spreadsheet – recruited me as a product manager, I soon was tasked with growing and managing virtually every function in the company save software engineering. It was delegate or die as my staff grew from one – me – to about 75 marketing and sales people, QA engineers, documentation writers, product managers, accountants, and even facilities management, as we had our own building. Learning to delegate became an incredibly valuable skills in my four venture-backed startups.

I developed a rule of thumb for delegation: delegate everything someone else could do better than I. That was the key to gaining leverage as my management responsibilities grew. Not having any individual skills – I wasn’t trained in engineering, sales, marketing, finance or administration – made delegation a lot easier. I was never tempted to try to do anyone else’s job myself. But I did see other managers who had never learned how to delegate and I watched them reach burnout as they vainly tried to do more and more themselves rather than delegating to their staffs.

Thus the Inc. article 5 Reasons That Entrepreneurs Fail to Delegate–and Fail to Succeed caught my eye, especially the very wise subtitle: Success in a new venture isn’t about how much you can do yourself.

Let’s take a look at each of the five reasons and as usual I’ll annotate them from my own experience.

1. Thinking only you can implement your dream idea

Most founders I mentor are bonded to their startup idea. And very few even think about building an organization, let alone delegating. I learned from VCs that they were investing in the team, not the idea, and building a team was job one for founders. Thus every business plan I ever did, starting with the very first one for Course Technology in 1989, carefully mapped out our hiring plan for the next three years. In knowledge businesses the vast majority – as much as 75% or more – of the operating budget goes to personnel, recruiting costs, salaries, benefits, and overhead. Yet it continually surprises me that founding teams have a DIY ethos. I can understand why founders who come up with a great idea are frankly afraid to delegate, thinking only they can implement their idea. But they are missing out on, and what I learned early on, is if you hire only people  who are better than you are they will not only implement your idea but do a better job than you ever could. I was taught by the VCs that “A “players hire “A “players, but “B” players hire “C” players – out of fear of losing control and being shown up by their “subordinates.” Delegation means letting go. And counter intuitively, only by letting go can you transform your idea into a business that scales.

2. Being unwilling to take the time to explain and delegate needs

Unfortunately many founders operate on the old saw “If you want something done right, do it yourself.” They  are unable to trust their staff. Not only do they lose out on the incredible leverage that hiring great people gives you as a founder, by micro-managing they demoralize their team and can end up not only losing great people but by never actualizing their business idea. I found the best way to develop trust was to assign a small task that could be done fairly quickly with minimal resources , starting with job candidates. Great people rose to the challenge and were hired, others didn’t and were not. But the pattern was set: as their manager I would help them set goals, would get them the resources they needed, and would provide feedback and guidance when asked, but basically they were on their own to achieve their goals. And thus they owned the job, they weren’t just renting it from me. If employees act like owners your venture will succeed! The time you invest in setting goals, providing resources and offering feedback will be paid back 10X by teams that see you as their leader, not their boss.

3. Not trusting key team members to get required results

When we hired Howard Diamond as our VP of Marketing and Sales at Course Technology he built his organization around peer-to-peer management. Each sales territory had an inside sales person, a field sales person, and a customer support rep. The teams were compensated based on the results the team achieved. There were no individual goals. He used peer pressure to deliver great results. In the rare occasions when he hired someone who wasn’t pulling their weight the team let him know immediately, because they knew that hiding that fact would hurt them in their pocketbooks. Giving his regional sales teams autonomy delivered amazing results, but of course required delegating traditional sales management to his teams. They knew the results they had to deliver, but it was up to them to figure out how best to do so.

4. Having a lack of your own clarity about what it takes to succeed

Most of the founders I mentor are engineers. They like to build stuff. They know how to build stuff themselves. What doesn’t come naturally is helping others to build stuff. I find engineers often need a lot of coaching to learn how to provide their teams with the “what” and “why” of their goals, leaving the “how” to the teams. This requires focusing on results, not activities. Too many inexperienced managers focus too much on process and not enough on results and on the metrics they need to help their teams become self-managing.

5. Being afraid that delegating means losing control

Like any green manager I had this fear myself, but because it I was endanger of drowing in work if I didn’t delegate I was forced to give up control. Through my initial experience managing media professionals I learned that while I needed to hold my staff accountable it was up to them, not me, to get the job  done. The real trick is NOT to set goals for your teams but to help your teams set their goals in the context of the venture’s goals. Collaborating on goal setting is far more effective than dictating goals as teams will buy-in to goals they set with you.  Delegation requires trust and giving up control, but you will find that if you hire “A” players their drive and ambition will deliver results beyond what you ever imagined. Your management role may well become pulling your team back from setting unrealistic goals, not pushing them to achieve stretch goals you have set for them. Pull works far better than push when it comes to managing your staff and in selling to customers.

Delegation all boils down to leverage. You can get much more done through others than you can by yourself, which can be thought of as the defintion of management. Startups are expected to scale and grow rapidly. To do so you need to focus on what you and only you can do and delegate everything else. It’s scary, so start small with very short term projects to build trust and autonomy. Don’t expect that you can just hand your team their year-end goals and walk away. Create short term projects with accompanying feedback – I call this cybernetic management – courtesy of Norbert Weiner. I’ve taken his term  beyond communications and control in the enterprise to encompass communications, creativity, and collaboration. The cybernetic organization appears to manage itself, with a minimum of friction. Management thus can be “management by exception” leaving founders free to set strategy, manage their Boards, and otherwise focus externally.


Author: Mentorphile

Mentor, coach, and advisor to entrepreneurs, small businesses, and non-profit organizations. General manager with significant experience in both for-profit and non-profit organizations. Focus on media and information. On founding team of four venture-backed companies. Currently Chairman of Popsleuth, Inc., maker of the Endorfyn app for keeping fans updated on new stuff from their favorite artists.

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