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Millennial Series #4 – Knocking It Out of the Park

You’ve got a plan (more than half the battle done!) and a strong successor identified. Beautiful.  The job isn’t done yet, though. You also want to make sure that your plan is executed to your expectations and that your successor is going to be successful.  This is where you want to knock it out of the park and every little bit of support helps. As they say, the devil is in the details. Don’t underestimate any little thing that might help both you and your successor roll out a rewarding transition plan.


Now, whether your Day One for transition starts with the signing of a formal agreement or the day your successor walks through the door is up to you, the first thing you need to do is to make sure you have a game plan set out regarding communicating your transition strategy:

  • How and when you’re going to communicate to your employees about your plans
  • How and when you’re going to communicate to clients about your plans
  • When you’ll introduce your successor to clients
  • When you’ll let your successor fly solo with existing accounts
Getting the Buy-In

A big part of setting your successor up for success is introducing them to everyone who they’ll eventually be responsible for and making sure that your successor has their support.  We can’t stress enough how big this responsibility is for you as the business owner. It is your job to clear the road for your successor and establish that they are the next in line to the throne.  

Be prepared – this might not come naturally or easily.  Your successor is going to have to earnthe support for the long-term and prove themselves, especially to all your other employees that you’ve depended on for so long.

Validate Concerns

Don’t underestimate potential feelings of uncertainty by the rest of your team if your successor is shiny and new to your organization. Your team doesn’t know this person and they’re untried. Your job is to reassure your team, offer a private and sympathetic, but reassuring, ear to their concerns.  Make them feel as confident in your choice as you are. On the other hand, if your successor is someone who comes from within your organization, you may deal with other feelings by employees. Jealousy coupled with uncertainty or even outright hostility. Hopefully, you’ve selected someone who has played nice with others and has already shown the necessary skills required so buy-in from others is already a done deal. But be prepared just in case.

The Softer Side of Preparation

Your protege can do the math, their spelling is on fleek (go ahead, ask a Millennial what it means), and they’re ready to immerse themselves in the industry.  BUT people have their own way of doing things (the nerve!). You have a preferred way of managing your business, employees, accounts, and vendors. Now you have to train your protégé in the ways that made your business successful and worthy of a decent valuation and sale.  You’re going to have to harness all of your skills as a mentor to help them navigate new waters on actually “doing business”. Sorry, you’re not getting off lightly here.


Hear us out on this one.  We’re not talking about signing them up to learn which fork to use (although if their table manners resemble ravenous wolves this is definitely something you want to coach them on!), we’re talking business etiquette.  

We’ve all heard (and are possibly even guilty ourselves of saying them) the lamentations that the younger generation just doesn’t “get it”, that they’re entitled, they’re rude, and any other social indiscretion we can heap onto them. Most times (we hope) a faux pas is committed because of ignorance rather than maliciousness. In this case, it’s better to get ahead of potential blunders and embarrassment to guide your novice past what could be a big stumble. This is where your years of experience are going to help – let you be the cautionary tale on what not to do.  Use your examples and explain why you do certain things a certain way – salutations, follow up communications, cold calls, holiday greetings, etc. These are the little things that have a big impact and can help build the confidence of your new rock star.

Emotional Intelligence

This is one of those skills that can be learned, taught, and honed. But why is it so important?  Because it means you can recognize emotions (what is triggering them in both yourself and others) and therefore manage them.  This little talent is what you would have engaged when disclosing your transition plans to your team and clients (scroll back up to our second paragraph!).

Psychology Today identifies three different skills that makeup Emotional Intelligence (EI):

  1. Emotional Awareness
  2. Ability to harness emotions
  3. Ability to manage emotions

Emotional awareness goes without saying.  If you can recognize when you’re having a temper tantrum, you can stop it and control your actions.   Harnessing emotions mean you take the energy from that potential tantrum and refocus it into a productive outlet like problem-solving (and removing the trigger for the tantrum).  Managing emotions means handling your own emotions and that of others in a positive and productive way. While this sounds manipulative, it really means being the cheerleader or the therapist for others.

Having a high EI also comes with a financial reward.  Leaders who lead through understanding and are more self-aware can actually incite greater productivity (a nice way of saying money) from employees.  People want to, and will, go over and above for a leader who they feel connected with, who “has their back”, and who understands and listens.  

This is the skill you need to make sure your successor knows, that they practice and that they’re cognizant of at all times.  EI leaders inspire others, can improve engagement (and thus reducing employee or client turnover), and will build successful businesses.

The Hard Skills

These ones are little easier to wrap our heads around.  Give someone a tangible task to work on and complete.


We’re not going to start here by telling you to get them to “learn computers”. Remember in our first blog about Millennials we said they love technology? Here’s where you can speak their language and harness their love and aptitude for all things shiny and techy.

Listen to them on what they think you need. Set them forth to research and learn what is new and available in the industry (or can be made usable for your business even if it’s not directly related to insurance).  Get them to help bring the company forward to build efficiency and cost savings. This lets them have some skin in the game (they’ve contributed immediately and in a significant manner) and makes use of one of their key traits.

You’re not giving them tech skills, you’re giving them freedom and ownership to use it.

Continuing Education

There are the accredited industry courses that your successor absolutely must complete to stay current and licensed, but learning doesn’t stop there.  Many courses have validity in the business world.

So what do you want them to know that you can’t teach them?  

  • Business writing. A great skill to learn to succinctly communicate to clients and employees.
  • Human Resources. If you don’t have a designated HR person, knowing the fundamentals will go a long way for any business owner.
  • Business Ethics. We’d like to believe this one isn’t needed but this can go a long way with keeping everyone on the straight and narrow, especially when dealing with sensitive client information.
  • Tax Regulations. Anything government related (apart from industry-specific requirements) that can affect your business is always worth keeping up on.
  • Accounting and Finance.  Everyone should be able to look at their own books and know what’s going on.
  • Marketing. So tightly aligned with Sales that Marketing is a skill that every owner should have a basic understanding of in order to promote and drive inbound interest.
  • Public speaking. Your protege might not be making any TED talks, but training here will help with our next skill – networking.

The list is endless.  Think outside the box and encourage your successor to do so as well. Knowledge is always power!


Gone are the days of the three-martini lunches, but networking is still the valuable entity in owning your own business – or just doing business.  Look at the proliferation of LinkedIn. A younger successor, however, might need some guidance on where and how to meet new colleagues and business prospects face-to-face.  Give them some organizations, from the national to the local level, to become a part of. Business Improvement Associations are the bread and butter of networking at the local level. Get them involved.

Make sure they aren’t limited to just our industry.  If the bulk of your client business is done on the golf course, make sure they own clubs. Get them where the clients are and make them part of the community.

When their ready to expand the business (because the assumption is already made that they will be a success based on the groundwork you’re laying for them), get them to join a marketplace like FindBob to find other practices to do business with.

Methods Are Flexible, Goals Aren’t

At some point, you’re going to have to recalibrate because stuff happens, things come up, and most importantly, we’re dealing with humans and let’s be honest, we aren’t always rational!

Giving your successor a solid plan for transition will give confidence to them, your clients, your employees and you.  You’ll sleep better knowing the business you worked so hard for is in good hands.

Good luck!

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