Do you want to say No to your boss but too often end up saying Yes? Some of my coaching clients struggle with this scenario. Recurring patterns of behaviour can lead to unhappiness, demotivation, and stress. It’s a potentially slippery slope towards the exit door, by choice and sometimes not. How can you reach a win-win situation with your boss more often?

Analyse the context

Here are a few reasons why it can be difficult to say No:

  • My boss reacts badly to challenging his or her authority.
  • The job will be more difficult/affect my career if I don’t comply.
  • I default to being helpful/passive/aggressive.
  • I don’t know how to deal with it.
  • It’s my fault because I’m new/too junior/inexperienced/lack confidence etc

A lot depends on the context. For example: 

  • Is your boss’s request part of a consistent pattern of behaviour?
  • Is it an occasional request?
  • How urgent and important is it?
  • Is the relationship with your boss trusting and warm?
  • Is the relationship distant and formal?
  • What personal and professional problems or inconvenience do the boss’s demands cause you?
  • Do your boss’s demands clash with an event/situation in your personal life that is more important to you?

7  Win-Win Strategies

From a career perspective, ask yourself how you can best support your boss without damaging yourself and the relationship. Here are 7 strategies to consider: 

  1. Check assumptions. Don’t assume your boss is aware you are unhappy about the situation. 
  2. Deal with the issue, not the person. It’s tempting to get personal and that’s when emotions can get out of hand. Keep things objective and focus on the facts.
  3. Be assertive. If it’s part of a pattern, explain how it makes you feel, the impact on your performance, the cost to the business, and discuss how both your needs can be met. Being assertive is about standing up for your needs and taking account of your boss’s needs. Get a different perspective by stepping into his or her shoes for a moment.
  4. Find alternative solutions. For example, if it’s a one-off or rare, can you arrange for someone else who is just as capable and available? Or, move your social event (if possible)?
  5. Negotiate. Sometimes, it’s a trade-off. For example, in return for saying Yes, you negotiate with your boss to promise something that you’ve been wanting or needing. Or, vice-versa, and you offer something of greater benefit to your boss in return for not being able to meet the request on this occasion. Establish some give and take.
  6. Revisit your role. If it keeps happening, get greater clarity on your role from your boss and agree on mutual expectations.
  7. Preventive action. Help your boss be more efficient by finding ways to help prevent last minute requests. Discuss different ways of working together.

Prepare beforehand

Raising the issue calls for preparation before the discussion. Here’s an 8-step structure for thinking through your approach to managing your boss:

  1. Name the issue and give a specific example that illustrates the behaviour or situation you want to change.
  2. Describe your emotions about the issue.
  3. Say why it is important to you and the impact.
  4. Talk about the value of your contribution.
  5. Acknowledge your boss’s needs and say how you wish to resolve the issue.
  6. Ask your boss to respond to your views and how they see things.
  7. Use questions to move to resolution
  8. Reach an agreement on the issue and agree how you will hold each other to account.

Be courageous

One of my coaching clients didn’t like to say No to her boss because she felt too junior and was eager to please. So, she said Yes every time at a cost to her personal life and job fulfillment. Through coaching, she reframed her position and the contribution she makes. She plucked up the courage to make her boss aware of her dissatisfaction and where her abilities could best be deployed. Their relationship became more open and they worked together on more effective planning and prioritising.

Do you say Yes too often and suffer for it? How and when will you change things?