Entrepreneur Must Define New Role Before Bringing In a Second-in-Command


TEC Worldwide is an international organization of more than 7,000 business owners, company presidents and chief executives. TEC members meet in small peer groups to share their business experiences and help one another solve problems in a round-table session. The following questions and answers are summaries of recent TEC meetings in Southern California.

Question: My first attempt to hire a president to handle day-to-day responsibilities (so I could step back and focus on strategic issues) was a disaster! We constantly butted heads, he kept trying to undermine my authority, and the employees never accepted him.

I fired him and now I’m stuck with the day-to-day again. I want to hire another “No. 2,” but this time I want to do it right. Any suggestions?


Answer: Welcome to the club. More often than not, founders of entrepreneurial companies fail in their initial attempts to bring in a second-in-command. Although the hired gun always takes the fall, it’s usually the owner who shoulders most of the blame.

Management consultant Steve Coffey of Coto de Caza has worked with a number of Southern California business owners who wanted to integrate a president or chief operations officer into their organizational structure. He identifies the most common causes of failure as failure to define the owner’s new role in the business, lack of clear boundaries for the newly created position, poor communication between the owner and the No. 2 and the owner’s inability to let go.

To avoid these pitfalls in your next attempt, identify your objectives. What specific outcomes do you expect to achieve with a second-in-command? How will that allow you to do your job more effectively? How will it benefit the company and your bottom line?

Don’t even think about hiring someone until you can answer these questions in a way that makes sense for the business. Never bring in someone just because you want to “get some things off your plate.”

Define the No. 2’s role before you hire. Do you want a president, COO or CEO? Do you want a leader (someone who will work with you to create the vision, strategy and corporate objectives) or a manager (someone to steer the company on the course you have already set)? The more ambiguity in the role, the more you set the person up to fail.

Get clear on your new role. Identify a driving need of the business that you alone can fill, such as new product development, maintaining customer relationships or making acquisitions. More important, how will your efforts in these areas improve the company?


Establish a regular, formal communication process with your new hire. Meet at least once a week to review expectations, identify issues, problem-solve and provide the necessary support.

Finally, take a hard look at yourself. Are you really ready to share responsibility? Can you live with the fact that people will no longer come to you for all the answers? Are you fully prepared to accept your new role in the organization? If not, you’re probably not ready to hire a No. 2 and should consider other options for your organizational needs.

Q: My small company has grown to the point where we need strategic planning, yet neither I nor my managers have much experience in this area. I’m afraid we might do more harm than good. How can I introduce strategic planning into my company with a minimum of risk?

A: Most Fortune 500 companies have huge departments to handle the strategic planning function. Some have entire divisions that do nothing put plan. Fortunately, however, you don’t need a Harvard MBA or million-dollar budget to chart a course for your company’s future. For small, growing firms, the simpler you keep the process, the better.

There are many systems and methodologies for strategic planning. At their core, however, they all address three basic questions: Where are we now? Where do we want to go? How will we get there? For most entrepreneurial firms, strategic planning need not get any more complex than that.

That said, here are some recommendations for your first time around: Go off-site for one or two days, so you and your team can focus on the planning process without distractions or interruptions. Use an outside facilitator--someone who has no stake in your plan or its outcome--to guide the planning process. Conduct a detailed SWOT (Strengths, Weaknesses, Opportunities and Threats) analysis, gathering input from as many sources as possible (employees, customers, vendors, etc.).


Based on this analysis, develop two or three major strategic initiatives to move the company forward. Don’t dilute your resources by trying to tackle too much at one time. Keep the plan simple. Employees at all levels of the organization should be able to understand the plan.

Build in accountability. Make sure every goal has a date for completion and someone who will be held accountable for getting it done.

Keep in mind that a strategic plan is merely a compass to guide your company, not a concrete path that leads to only one destination. Build some flexibility into the plan, review it on a quarterly basis and make adjustments as you go along.

As you and your team get more comfortable with the planning process, you’ll get increasingly better results.


If there is a business issue you would like addressed in this column, contact TEC at (800) 274-2367, Ext. 3177. To learn more about TEC, visit