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My boss is on the naughty list!

Compiled and edited by Julie Tereshchuk


Dear Mentors,

A year ago, I thought my boss was on the nice list. Turns out, despite her promise to provide me with on-the-job training opportunities to further my career and gain wider business skills, she’s on the naughty list. She owns the small company, and we’re a lean team, so I understand there are limited resources. But, I’m getting frustrated and disappointed in the lack of progress and response to my reminders about our initial plan. Do I cut and run or persevere? (She’s not all bad!) If I stay, how do I improve things?


Disappointed Elf


Dear Disappointed Elf,

My advice would be to make a formal appointment to meet with her. No need to explain in advance other than that you would like some time to discuss your role and your future at the firm. No more.

Then, I would spend some time writing a brief objective overview about the position; research its market value and outline the offer that was made before you accepted the position. When you sit down with her, start with something positive like: “I’m really enjoying the work we do and learning from you.” Then go into, “However, I would like to discuss with you the offer you made to me before I accepted the position to provide additional on-the-job training and to expand my business skills. It’s been a year now and my learning has been limited to (explain) … This is what I would like to see in terms of further training (explain) …”.

It is important that you keep the conversation objective and unemotional. Make it clear that any growth you gain will also be of benefit to her and the firm. Above all, suggest a solution – what are you asking her to provide rather than simply saying “You promised me some training”.


Jane Baxter Lynn


Dear Disappointed Elf,

With harried bosses, it’s always a good idea to frame your suggestions, requests and ideas in ways that help the boss and the business. Do the legwork and make it easy for them to say yes.

For example, “Dear boss, it’s obvious the load of xxx has been crushing over the last few months. I know I could take some of that work off your shoulders once I finish this training class I found online. Can I sign up to spend 2 hours a week moving forward with this training? It only costs X and I’ll be able to contribute more to the business in just 6 weeks.”


Instead of this (an extreme, but sadly real-life example): “Hey boss, I’m still waiting for career advancement. When will you make that happen?”

Good luck and happy holidays!


Sandra Kleinsasser


Dear Disappointed Elf,

You might be able to create your own Holiday Magic with some smart thinking and negotiating.

Take a look at the future projects you will work on in the next year and determine if there is an opportunity for you to add value to a project, especially if you have acquired a new skill. If you are serving clients, then ask your boss if your training can be built into the next project fee your company bills that client. Alternately, you could ask for paid time off for a training, even if you are paying for it yourself. You could look for a class or conference that benefits both you and your boss and then suggest that you attend it together (because then it is team-building and a training).

And, don’t discount learning from meet-ups, peers and free online or low-cost classes. Lastly, track the date of  WCA’s Get Smart and put it on your calendar once the 2020 date is released.


Anne LasseigneTiedt


Dear Disappointed Elf,

You’ve reminded her more than once, so I wouldn’t recommend bringing it up again. I would encourage you to inquire with your network about employers who offer training and maintain integrity in honoring their offered benefits. If you’re inclined, reach out to employers and management with the best reputations to request informational interviews. And if moved, make a move. Owning a small business may be quite challenging, however, honoring a promise should not be so.


Christine Moline


Dear Disappointed Elf,

I recently took the only remaining seat at a business event, only to discover I was sitting beside someone who’d fired me during a very difficult period of my life. I’d held a grudge against her for years, though as time passed, I’d gained some perspective on the situation.

Running a small business leaves little or no time for the rest of life, and the financial pressures are tremendous. Employees expect the boss to appear in a good mood, bring in new business, the occassional box of cookies — and meet payroll every two weeks.  So we started chatting. She’d lost her husband, scaled back her business and was delighted to see me. Moral of story: We’re all human, bosses especially. Assume good will and keep asking for what you need. But consider there may be other ways to achieve it by taking a class, seeking out a mentor or joining a professional organization.


Raye Elizabeth Ward


Dear Disappointed Elf,

My advice would be two-fold: first, find a way to align your goals with hers. Can the training you seek lead to less work or more profit for her in the long term? See if you can suss out her hesitation and address it head on. Maybe she’s worried that training you will lead to your departure or asking for a raise; address her concerns if you can.

Second, if you can’t get her to help with training, take matters into your own hands! There are TONS of opportunities for training and professional development (ahem… WCA!) and you can take ownership of your training and move in that direction. See if she can pay for your membership or a class here and there. At the very least your boss should allow you to duck out for a workshop at lunch or spend some time with an online webinar that would enhance your skills.

If she won’t support you or allow you even the time to learn on the job, consider your long-term plans and have a serious talk with her about your goals. Any boss with an employee they don’t want to lose should be willing to help them grow; if not, it’s time to explore your options.


Jenny Magic