Career move: Are you ready?

You know you’re ready for a change – a new challenge, perhaps a move up the career ladder or maybe a new location or industry.

Before you start putting out feelers, stop. (Yes – stop!) A little bit of groundwork can make a career move much more successful.


Take some time to review: 

  • What things do you love?
  • What don’t you love?  
  • What excites you?
  • What wears you down?  

Be completely honest! You’re not going to show this to anyone else. You don’t have to be seen to be somebody you’re not, nor do you have to try to please anyone else. This is a time for transparency and brutal honesty with yourself.  

Next, divide a notebook page in two columns and title one, “Love It” and the other, “Leave It”. At the end of each day, for a couple of weeks, go through your day and jot down things you did and things you avoided under either the “Love It” or “Leave It” column. 

After a couple weeks, you’ll have a pretty good list of things that drive you and things that wear you down.  (You don’t have to put everything on the lists – but if it remotely charges you up, put it under “Love It” and if it remotely bothers you or wears you down, toss it under “Leave It.”) 

We’ve also created a downloadable worksheet

Depending on the rhythm of your annual work cycle, at the end of the couple of weeks you may need to look ahead and think about what’s coming up. Consider whether you:

  • Love the year-end financial stuff? Add that to the list.
  • Love that you get four weeks of vacation? Add that to the list. 
  • Dread having to write the annual staff performance reviews? Add it to the list.
  • Know that you need an annual salary of $X? Add what you need to the lists as well – bonus, overtime, company car, expense account – just remember to differentiate between a want (would be nice to have) and a need (must have).

Think about what else you love in life. Perhaps these other things don’t immediately or obviously translate to a career move but then think about WHY you love them. Does the why translate? 

For example: 

I love being on the board of XYZ Non-profit because my role lets me see the big picture.

I like volunteering at the food bank because I can see the effect we have on people 

I like coaching sports because I like seeing the outcome of things.

I like having dinner with my kids every night.

Give some thought to what your “ideal” career move looks like and write it down. Read it a day or two later and edit it based on your gut reaction. 

So, a draft might read something like:

I want a role that lets me see a big picture – so something more tactical or strategic, where I can see an outcome for people directly. I enjoy sales but not the daily financial pressure to deliver, deliver, deliver.

When you’re thinking about your ideal, forget about “forever” and focus on the next few years. What would be ideal for now? Some of us of a certain age tend to look at career moves as rare and all-defining when, in fact, it could be an interesting step to a future opportunity.

I know that many of us think only of moving UP the corporate ladder, but there are times when a lateral career move makes sense. While you’re looking for opportunities, weigh all your available options. 

Go through your address book, and list 20-30 people you would feel comfortable talking to about your desire for a career change. They do NOT have to be people in your preferred industry or people who hire others. Schedule a coffee talk or phone chat with at least 15 of those folks.  

The goal is going to be to share with them what you’re looking for and why. You want this conversation to spark them thinking about who they know who might know someone who could help you find a new career opportunity. You see, you’re expanding your network by starting with people you know. 

There’s a really good chance the next person to hire you isn’t already in your address book, but there’s a good chance they’re in the address book of someone you know. 

When you meet your contacts for coffee, bring your goal statement and be able to speak in detail about it. We’ve included room on the downloadable worksheet for this information too. 

Telling someone over coffee that you’re looking for a job doesn’t accomplish much. They hear you but don’t see a role for themselves.  

Be Clear

You’ll want to be clear on a couple of things:  

  • Tell them what are you looking for in a career move
  • Share with them what are you good at (see the lists you created) 
  • Ask them if they can help you find something – or if they could refer you to others who might have a connection to something interesting

What about your current employer? If you really love your current employer, but you’re just not loving your current role, putting the same strategy to work within your current organization can work well, too. 

Build a network internally and use the same techniques of figuring out what you like, what you’re good at and seeking out a new opportunity. 

If you’re looking outside your organization for a new career opportunity, give some thought to when you want to share this with your employer:

  • On the one hand, you may work in an organization that won’t take it well when you tell them, so you may need to delay until you have a solid offer. 
  • If you have a good employer, they may want you to stay and offer to work with you to figure out how to bring out your real strengths with new responsibilities.

If you don’t share the information right away, prepare a response in case word gets back to your boss or employer that you’re looking for work elsewhere. Outline why you’re looking and how you would like to contribute more. 

As you explore the possibilities for a career move, remember this is about finding a good fit  – the best fit. You’re courting and being courted to see what opportunities are out there and you might land something really exciting. It’s good practice to consider your next career move at least once a year. 

Keep your eyes wide open to the fact that maybe your current role or company might turn out to be your best option right now. If there is some part of your job that made you think you needed to move, then you can try to do something to improve that part (rather than throw the baby out with the bathwater as they say!). Often a damaged interpersonal relationship is the motivation to move to a new workplace, but changing your perspective could change your career.

Coach’s Questions

What are your feelings about a career move? What can you do this week to figure out your ideal career move? Are there opportunities that you know that others in your network might be interested in? 

How to disagree with your boss

I remember vividly as a young professional a time when I had a dissenting opinion about an important issue, but hesitated to offer it. 

The problem was that I didn’t feel encouraged to give an honest opinion if it conflicted (and it did!) with that of the people more senior to me at the time. The boss was defensive and took disagreement as some sort of insult or insubordination. And so, of course, he often heard what he wanted to hear, not what he needed to hear.

It’s not uncommon. We’ve had clients share with us that they don’t know why their team members won’t tell them the truthand others who struggle to be candid with their bosses or board members. 

If you’re the leader seeking good information to inform your decision-making, you can learn how good leaders handle honest feedback and criticism and strategies for making the best decisions.

When you’re on the other side of things and disagree with someone you report to, it can be challenging to figure out how you can share your opinion without watering it down (and without needing to duck and cover!). 

Disagree with your boss

Here’s how you can disagree with your boss with less worry about being blacklisted or fired:

  1. Line up those ducks of dissent beforehand.
    To be able to disagree, there has to be trust. Strong, respectful relationships allow people to contribute and communicate truth no matter where they are in the office hierarchy. This is why when we work with teams, we help them learn to build conflict (the good kind!) in the workplace.

    Instead of waiting for a time when you’re in a meeting and wonder whether you can share your thoughts freely, have that conversation with your boss when the stakes are low. Find out how your boss feels about dissenting opinions. How should your team handle and manage disagreements when the stakes are high? Having established ground rules about what healthy conflict looks like and how to encourage a culture that allows for healthy debate leads to better decisions and successful organizations.
  2. Read the situation and strategize.
    Timing, as they say, is everything. If you have established strong work relationships, sharing frankly with your boss is easier than it can be otherwise. Additionally, different personalities will take information better in different waysboth WHAT is delivered (facts and figures vs feelings) and HOW or WHEN it is shared (for example, in a group or privately).

    You might have very valuable insight for your boss, but it could be that if you share it in a public forum that boss will feel undermined and embarrassed. If this is the case, you’re better to ask to meet with your boss privately after the meeting (I have an idea to share with you offline about this situation. Do you have a minute to chat?)

    Perhaps it’s an important meeting with a variety of stakeholders present, but the tone is more one of brainstorming for solutions. In that case, contributing your radically different perspective in a respectful way (You know, it occurs to me that we could take a completely new approach and do this…) could be very well received.

    It can also be helpful to remember that other people are sharing ideas that they feel strongly about. Acknowledge the contributions you agree with (While I agree that X is an important consideration, and as you say that Y is another factor we need to keep in mind, I feel that….) and ask questions about the things you see as potential challenges or barriers (I hear what you’re saying about Z and that is valid, but I’m wondering about ABC. How would we handle ABC?).

    When you are able to stay collegial and collaborative, it helps to keep the focus on finding solutions rather than winning an argument. Asking questions is a way for you to ask for the opinions of someone more senior than you and offer your own reservations about a topic in a respectful way.
  3. Make your intention clear.
    Even if you have a good relationship with your boss and your work culture encourages healthy conflict and sharing of ideas, it helps to frame your contribution to the discussion in the right way.

    When there is tension or if things get heated, it’s human nature for people to feel defensive about their own positions. What is the goal that everyone hopes to achieve? Preface your idea as a way to meet that goal. This way, even if yours is a dissenting opinion, it doesn’t threaten the position that your boss cares about.

    “I know we all want to land this big account. I feel that we could still do this with what you’re suggesting but we need to consider X, Y, and Z before we tackle what you’re proposing.”

    It’s crucial that, especially when you don’t agree, you still show respect. A boss who feels you are respectfully sharing a counter-opinion will be much more likely to listen to understand (not just to respond!) than one who feels under attack.
  4. Ask for permission to speak freely.
    Some discussions in the workplace are much more delicate to navigate than others. It could be that there is a decision to be made around a disciplinary matter or an ethical decision.

    These are times when even if you’ve earned trust, it’s good to not only make your intent clear, but to ask for permission to share your thoughts honestly as a sign of respect.

    “I have some ideas about this, but I don’t want you to think I’m trying to undermine your position. I don’t feel right staying silent about this either because it’s crucial we make the best decision for the company. May I offer my opinion for you to consider?”

    When you negotiate the terms of sharing your truth, it’s less likely that your boss will mistakenly take your dissenting opinions as disrespectful or threatening.

In a perfect world, of course, your boss would love your ideas and take your opinions into consideration. If this is not the case, you need to respect the final decision and fully get behind it — that means doing whatever you need to do to make it successful (and not saying I told you so if down the road it turns out you were right!).

The good thing is that when you are able to disagree with your boss or the board and have your say, you’ll never regret that you didn’t say anything that could have changed the outcome. Not only that, but your boss will know that you can be counted on to say what you think courteously and respectfully.

Coach’s Questions

Have you ever disagreed with a boss or superior? What would you do differently to disagree with your boss now? Do you think your team members feel they can disagree with you?