Keeping healthy relationships throughout your transitions

Problem:  it can be challenging to talk to loved ones, business associates, or employees about an upcoming transition.  This can result in delays, anxiety, and sometimes rocky transitions.


In this post, I want to share a few common scenarios about people and their upcoming transitions.  I think most people will relate to either of my examples. I'd then like to provide a few key principles to practice and employ when planning for and conducting a life or business transition.  I really find these to be First Principles and if employed in concert and with integrity, can make for well coordinated and meaningful transitions for everyone.

Example 1: Pam has owned and ran a flower shop for 20+ years.  Several of her employees have been with her for about 10 years and she feels quite close and loyal to them.  None of them are nearing retirement age but they are also in situations where continued employment with the floral company is important.  Pam's been thinking about retiring and moving on to something new, and has started working with a financial planner and a transitions consultant to get things in order in the best ways possible.  She's very concerned about the prospect of retiring and what the effect on her employees will be.  She's not certain about the best timing, format, and resources she should gather to really make this part of her transition as smooth and comfortable for everyone as possible.  She already has a few interested buyers who really remind her of herself in her younger years and thinks they'll be a great fit for the company.  When should she talk to her employees? What kinds of resources would be most meaningful to have prepared for them?

Example 2: Sam has been working as an engineer for 15 years across a variety of places inside his company.  He's put a lot into his work and feels he's been of great value to the company.  However, in the last few years, he's felt he's plateaued from a learning perspective and also from a salary growth perspective.  He has no interest in management as a way to increase his learning and pay.  He see's a lot of people leaving the company to explore other firms they work for in their career fields and is at the point where he wants to make that happen as well.  He's not sure about how to talk about this with his wife and kids and what kind of involvement they can have that will make it work most beneficially for everyone.

First Principles

In my previous work as an Industrial Engineer and Continuous Improvement Consultant,  there was always a lot of talk about how people fear change.  That conversation had many forms but it really boiled down to what people perceived or described as a fear of change.  I never really bought into that.  There are a lot of other folks out there that have this same perspective I'm going to describe but here's what I think:  People change all the time, every day there are changes to what they expect about how their days are going to play out.  It rains instead of shines, they hit traffic and have to divert their route, or their child wins an award at school and they change dinner plans to celebrate. I would describe it like this "People don't fear change, they Fear BEING changed", and in particular, by other people around them that they are familiar with to some degree.  When change is proposed and the gears start turning, all kinds of baggage comes with the change like ones framing of the events, the perception of other peoples intentions, and whatever sort of relationship they may or may not have with others involved with a "change".

These issues are similar to when you are planning a life or business transition.  No person or business owner is an island unto themselves and they have relationships and influences with a variety of people and organizations.  For business owners that are retiring, some of the most challenging to deal with can be a general sense of loyalty to their employees as well as their relationships with long time employees and for people changing careers, it's often associated with their partners and children (if they have them).

What follows are a set of First Principles - basic and fundamental mental models to employ when undertaking a transition:

  1. Allow for ample time for the conversation to unfold, if at all possible.  This can be 2 years if necessary or shorter in various cases, but overnight will obviously be a shock to everyone and will most likely result in a lot of unnecessary strife and conflict.  This gives time to adapt to the coming changes and engage with them in healthy ways.  Provide space and time for feedback to take place.

  2. There is no "Best Time" so act accordingly. I think the most important thing to be clear about before you start a conversation with employees or spouses is to have really thought through and understand your sense of "Why" you're doing this. Explore this in a variety of ways and really get down to a few fundamental reasons that they will easily relate to in some way. Don't skip this step or give it a cursory thought.  People involved in your transition may have a lot of questions and concerns about "why now?" and "aren't things going really well, why would you want to change?", etc.. I'm not saying have a reply for everything but demonstrating you have a fundamental set of "Why's" shows a lot of commitment and thought given to what you're going to do.  Additionally, it demonstrates a respect for their potential concerns by you being able to have a meaningful conversation with them about it and that you've considered their perspective.  This isn't foolproof but is vastly better than some superficial or overly simplified answers to "Why".

  3. Be open and honest but not overtly and brutally so. Take the "Outside View" and understand others perspective but know also that not everyone needs to know everything about what you're planning nor would it be useful to them.  Basically, answer questions when asked but it isn't necessary to share ALL the details of your why's, goals, plans, etc. with everyone.  I found in my work, most often, that some people are overwhelmed with how much detail there can be while others go into Analysis overdrive and want to question everything or contribute in ways that aren't helpful.  This is entirely subjective and super squishy but there is a balance to be had.  Don't lie about anything you're planning on but also don't describe everything about it as well.  Honesty is critical and I also suggest an "open door" policy meaning you have explicitly stated that people can come to you and have a discussion about questions or concerns and you'll see what you can come up with together.  This is about integrity coupled with a little "people wisdom", a great character trait in any time but even more important in times of transition.

  4. Provide resources to help reduce uncertainties and fears about the transition:

    1. First off, have key points, goals, and milestones available to share.  Only include information relevant to all your stakeholders.  Some things will be too complicated to share with kids so ensure you garner your conversation to the unique communications needs of children.

    2. To help with the big picture and long term, a few key resources can help people feel stable in times of change either for employees or a life partner:

      1. Financial Resources: provide avenues and even fund some level of financial planning or education for your employees or have your partner participate with you in these activities.  Employment speaks to so much in society and at its root can be security, protection, and even deep feelings of life and death when it comes to the ability/stability of housing and food for yourself and your family.

      2. Career Counseling: this could help even for you but providing the avenues and perhaps funding for this sort of thing can help people understand their options but also help them feel empowered.  Even if continued employment for your employees is nearly certain or if your partner is concerned about backup plans or alternatives, having some level of counseling in this area could really help.

      3. Mental Health Resources: sometimes anxieties and fears can boil over and impact you, your business, your spouse, or your kids.  Having professional support in times like this can really help.  Even in long term preparation talking with a professional can help you explore the roots of fears and anxieties, assumptions you might have, and ways you can help yourself and your relationships stay healthy through any transition you may be working on.

  5. It probably isn't as big of an issue as you're making it out to be.  Are you making a mountain out of a mole hill? I've observed in numerous relationships and planned transitions, that people often overestimate the difficulty of having conversations about their transitions.  This can perhaps come from people thinking way too much about other peoples perceptions without having much real data to back this up.  If your life relationships are strong and trust is long established between the parties, then the conversation probably won't go as poorly as you might perceive.  Some of this is another flaw in our operating system is our brain trying to anticipate pain and regret and so will do it's utmost to convince you to not pursue your intended course of action.  This characteristic came to be a LONG time ago for vastly simpler circumstances but we need to understand where it might be coming from when we're dealing with more complicated (and likely much less physically risky!) modern scenarios like a life or business transition.  The same sort of thing goes for business owners.  I've found many are worried, rightfully so, about their employees and want to ensure their transition is as smooth as possible for the employees as well.  However, I've also found many are spending a lot of time thinking about it and not taking some first steps to address it.  Simply writing down your perceptions can be helpful, as well as crossing off the ones you come to find may be overblown!  Next, is having a few candid conversations with your closest employees will help you get a better idea of how things would go as well as start to cultivate trust and relationship for your transition.  Then a wider conversations, with the above Principles in mind, can help to start and continue the conversation until your transition is complete.


None of the above suggestions are easy for everyone to take on and some of them may be common sense to many.  I can say, however, that doing nothing until the last minute, prolonging the conversations, or staying nebulous and non-specific in your relationships will likely only foment mistrust, misunderstandings, and create an environment that won't be conducive to a smooth and healthy transition.  I personally have practiced these principles in my previous career and in my numerous life transitions at home and have found that, when used in concert, they can really alleviate fears, decrease stress, and ultimately result in a smooth transition for everyone.