The blessing and curse of the longest-standing employee is that they can be equally harmful and helpful to the growth of a business. And unfortunately, they are rarely conscious of how they contribute to being a curse.

The longest-standing employee doesn’t become the “problem child” overnight. It is a compounding effect. We make a new hire. We start to charge more. We stop taking clients’ calls 24/7. We set boundaries and standards and start holding everyone accountable (including the longest-standing employee). We begin to track and measure everything we do. We begin to question why we are doing what we are doing – and if what we’ve always done is working any longer.

ID-10045221We start acting and operating like a business. And the veteran employee reflexively reacts, and not necessarily in a positive manner. Our once-superstar, lifeline employee starts to show up in a combative, negative manner.

I like to believe this is because they have your best interests at heart. They’ve been there for a long time, experiencing the good, bad and ugly in all areas, from cash flow, clients and personal crises, and the list goes on and on. At the core of the now-combative, negative tonality is the following thought process: “We’ve worked so well and so hard to get where we are, I will be dammed if I will allow this business to crash and burn.” They are coming from a genuine place of protectiveness and honor.

But the truth of the matter is, change is inevitable and necessary. Dan Sullivan of Strategic Coach says it best: “The tools that got you out of Egypt are not the same tools that will get to you the Promised Land.”

Change is not for the weak. Growth is no joke. And when you add the human element of it all, hiring and adding staff, that’s when it gets downright messy.

We are noticing more and more of this in our Team Empowerment sessions; when a business grows and the teams grow, the veteran employees often have a hard time. And they are totally unconscious to it. The mindset sounds like this: “When it was just him and I when we started this business and I was able to do the job of four people, we were making money, things were moving and grooving. These new kids on the block are suggesting stuff that we already tried, stuff that totally flopped. They don’t have the history, they are just here for a paycheck and they don’t take it as seriously as we do. They don’t understand the industry; our clients don’t like it that way. Our referral sources will never go for that.” You get the point.

Finding great employees is challenging for all entrepreneurs. Even if you manage to find good workers, keeping them is a whole different challenge. So investing in a long-term employee during the uncertain times of change is well worth the investment of coaching and guiding them through times of change (which will never stop, because we are growing). As a small-business owner, having long-term employees is vital for many reasons.

The longest-standing employee provides a solid knowledge base and an invaluable support system. They forever and a day have your front and back, they are willing to speak the truth and have the crucial conversations necessary in real time, they want to retire with you and will take a bullet for you. But when you start operating like a business, that isn’t enough to keep a longtime employee if you cannot coach them into the long-term vision and get them excited and fully onboard to do this. They can’t fake it and they can’t be half in. Their lack of commitment to our “new normal” will ooze out of them, and the other team members will sniff that out like bloodhounds.

The longest-standing employee can not only be saved but can soar with the proper enrollment, empowerment and guidance. To schedule your complimentary Team Empowerment Call to discover how to keep your team growing together, contact us at

THE fix my boss workBOOK



This workbook is intended to be used in conjunction with the book, "Fix My Boss" to cultivate respect, risk courageous conversations, and increase the bottom line. The exercises and activities provided will guide you through a step-by-step process of understanding, analyzing, and taking action to create positive change in your workplace.

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