Building Your Business Dream Team in 5 Simple Steps

By Nina Kaufman, Esq.

The blogger and former web designer, Jason Kottke, was quoted as saying, “I don’t think you’re a very good friend if you’re always being supportive. You also have to add criticism.” Put another way, if we surround ourselves with “yes-men” (or -women) we’ll never grow as business owners. And our companies will reach a certain level and stagnant there, if they don’t embrace the need for change.

Therefore, just as entrepreneurs need to delegate the tasks of running their business (if they want it to grow), they need to delegate what I call the “mirror, mirror” function. We need feedback from others. We can’t take only our own advice, or consider only our own viewpoints if we want to reach our fullest potential. Nor can our business grow if we don’t learn from other successful people. In short, we don’t have all the answers.


And business owners are unlikely to embark on the difficult, scary, and courageous process of change if they don’t have a “team” – a team of advisors and colleagues who help look out for your best interests. Who push you to stretch yourself past your comfort zones. That’s why it’s so important to surround yourself with colleagues who have an objective (yet supportive) attitude toward your company.

Whether help comes in the form of a Board of Directors (or Advisors), a Mastermind group, a CEO Roundtable, regular brunches with gal pals (or buddies), or family/spouse/partner, having an outside perspective on you and your company is crucial for your success and growth — both personally and as a business owner. We need the help of constructive criticism to point out our foibles, blind spots, and obstacles. So how can we create a team of advisors who will help us and our business achieve our dreams without tearing us apart in the process?

Here are 5 steps to get you started:

  1. Decide on the help you actually need. What expertise do you need most? Are you looking for specific subject area advice? Or overall support? Not everyone is suited to advise you in all areas. Some colleagues are better suited to bandying creative ideas back and forth. Others may have a particular expertise that you need to tap into only occasionally. Decide what you really need, first.
  2. Select the right people. Once you have taken the time to “know thyself,” you’re in a far better position to choose who can best help you in a given situation. Your “Dream Team” can take on many facets, as advisors come in many guises. In addition to those in your industry (because they have wrestled with the same issues), and those who are not (so that you can learn from other best practices), you also want to look for companies that are where you want to be in a few years’ time. Make sure you choose the right person for the right position on your team. The brusque, well-connected business owner may be great for introductions, but lousy for long heart-to-heart discussions about entrepreneurship.
  3. Make communication convenient. You may have a preference for in-person meetings, but that’s often difficult to arrange if you have to coordinate multiple schedules. Focus first on what’s most convenient for your advisor(s). You may find that they are more wiling (and available!) to talk to you if they can do so by conference call, rather than in person. Or, consider meeting with people one-on-one rather than trying to force a group dynamic.
  4. Prepare in advance. Be mindful of the time that your advisors are giving you. Just as you would not want your time wasted with irrelevant story-telling and background information, so you, too, should be sure to get to the point of your discussion, your issue, etc. The purpose of assembling a Dream Team is not to have them listen to your entire life story (that’s what therapists and friends are for); it’s to elicit their feedback to help you keep moving forward in a more positive direction. It helps if you have a clear sense of your business goals and challenges so that you can articulate them clearly.
  5. Expect “Tough Love.”” The purpose of a Dream Team is not to have a bunch of people sit around, stroking your ego, telling you how wonderful you are. It’s to get sound and realistic advice about how you and your company can grow. Sometimes, that can be hard to hear. The pet project that you have lovingly nurtured for the past year may get roundly panned. Don’t take it personally. Your advisors – especially those with expertise in your field – want you to avoid the problems, time-waters, and money pits that have befallen them. You want their honesty. Preferably, it’s couched in the form of constructive criticism (but if not, get over it).A healthy Team is an accountable Team. Be on time for your meetings or calls, and notice if your advisors are not. See if members of the Team (especially in mastermind groups) are open and willing to contribute. If not, don’t be hurt – just go through the 5 Steps to create the Dream Team for your success!

Have questions about working with Kaufman Business Law? This is the video to watch.