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The Boss You Didn’t Know You Missed

Do you remember that boss? The one who showed up at your door when you least wanted to see him/her, the one for whom you had a great nickname… Yes, that one – the one who always:


  • - Pushed you to do the things you didn't like to do,
  • - Scheduled (you thought, overscheduled) one-on- ones to remind you about those things,
  • - Pestered you about turning in your expense account within the stated deadlines.

As an entrepreneur, you treasure the independence you have to run your own business, and also realize that this independence comes along with the responsibility to do the things you don’t like to do. This is usually not a problem when you are starting out and growing from zero, as you have time and energies to make the business grow. However, as your time is taken up by running the business, you have less of it to grow it. This will usually look and feel like hitting a plateau, not unlike the one you hit when you are on a weight loss program or the technical resistance in a stock price (for those of you who like to day-trade). That is when you realize you need someone like that boss reminding you about the things that need to get done- maybe a coach or maybe, YOURSELF!


This plateau can materialize at a time when your business is doing OK, not great but OK. It is not losing money, it is keeping everyone of the employees somewhat busy, and you are drawing a decent salary. Despite this, you have higher expectations and eventually, you will want to be a good target to be acquired and cash in on what you’ve worked so hard to build.


So, how do you break through this plateau? The suggested approach is called: Back to basics with an Outside the Box twist. Let’s explore what this means and how you can implement it. Some ideas:


  • Fill the sales funnel with more prospects – Yes, it’s great to have a good client base, but natural laws of attrition always apply and you need to keep the sales funnel filled with prospects in order to maintain, and grow the client base. What does this mean to you now? Perhaps some structured time calling on prospects, specific social media campaigns directed at potential clients rather than your existing clients, speaking engagements, and, dare we say, calling on customers to ask for referrals.

    The Twist – Key Partners (people/companies) who can help you leverage your model. These normally include possible strategic alliances with complementary businesses, people who deal with your customers in a non- competing product, for example: If you are a professional services firm, you can collaborate with technology solutions that are complementary. These relationships can generate a one-to many source of referrals both for you and your Key Partner.

    Know your number – What was the reason you always brought home the largest bonus? You hit your targets. First of all, you had targets; do you have them now? How much do you need to sell/invoice to hit your budget? Oh, you don't have a budget, well sorry but you need one. The primary reason good salespeople hit their targets is because they have them. Sometimes the formality of a more structured environment goes away when we move to an entrepreneurial one, but some of that structure is fundamental to achieving our goals.

    The Twist – Targets are notorious for being miss-aligned with companies’ visions – they usually focus ONLY on closing, not in the quality of the client. Since your goal is to build a solid and sustainable company, you need to make sure you get good clients – ones whose contribution to your bottom line is commensurate with the investment you will make in getting them. In order to do this, you need to define what a ‘good client’ or ‘good transaction’ is so that you can keep your eye on the right metrics. One easy way to do this is to look through your current client list and find a few of these and figure out what they have in common so that you can look for similar traits in the new ones.

    Always be recruiting – Nothing slows you down like losing a key employee, reason for which you have to develop and maintain a strong bench. The employment numbers tell us that there is still slack and many underemployed people but the candidates that come in for job posting aren’t qualified.

    The Twist – Where to find these qualified candidates and why interview them when you don’t have a position open? Focus on finding your friends/associates/employees who are “Connectors” personalities, as per 'The Tipping Point' by Malcolm Gladwell. These people are usually very friendly, collect acquaintances, and enjoy making connections between them. Think about who those people are and reach out to them from time to time to get some names of possible candidates. Yes, you will get some unqualified people, but everyone you speak with (informational phone interviews) can also refer you to others and you will have a list of resumes to look through when the position does open up.

So, instead of hiring back your former boss (you’d be surprised but this does happen), make sure YOU embody the positive aspects of that role in your company.