Crucial Skills®

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Crucial Conversations for Mastering Dialogue

Speaking Up To The Boss

Dear Crucial Skills,

I’m trying to follow the chain of command in our organization when presenting ideas and suggestions, but the ideas seem to stop at my boss and never get to the people who would benefit from the suggestion or idea. My boss doesn’t like conflict or change, believes that getting along is more important than addressing issues that might cause conflict, and doesn’t see the value in sharing feedback unless it is to tell people they are doing a good job. How can I motivate my boss to take action on ideas presented to him to improve our organization?


Trying to Address Change

Dear Searching,

You are not alone in feeling stuck in this situation. Many would agree that influencing or motivating upward is a tough challenge. It’s tough to speak to leadership about behaviors that are negatively impacting the quality of work or the quality of work life. It’s tough to speak up about ineffective systems or stifling bureaucracy. It’s tough to tell your boss that you have more on your plate than you can do without feeling like a whiner. It’s tough to speak up when your boss overtly or subtly makes it clear that he or she does not appreciate you speaking up. And a key word here is boss—the person who can impact your ability to make your mortgage payment next month. So, it’s tough. I know that. I’d like to share some advice I’ve formulated over the years.

1. Frame the challenge in the best possible way. This is, of course, a variation on the crucial conversations principles: Master My Stories and Make It Safe. Start by asking yourself, “Why would a reasonable, rational, decent person (yes, your boss) act this way?” Why is he not passing ideas on or not encouraging or inviting others to speak up? What would make it safe enough for him and yourself to have this conversation? Make sure that you clarify Mutual Purpose and are prepared to be very respectful when you bring up the issue. You want to make sure you come across as curious and helpful rather than frustrated and judgmental. Also, don’t speculate and focus on the possible negative outcomes. We often exaggerate possible negative consequences and underplay the positives. That strategy causes us to vote for staying silent—thus voting for the status quo.

2. Talk about the right issue. In tough situations, we are often tempted to bring up a simple, easy topic and not the real one. In your particular case, the easy issue is that you made a suggestion and it wasn’t passed on. The real issue is that your boss has a pattern of not passing on ideas and that means that you and your colleagues face the same problems at work week after week. The real issue may be that you see yourself and others becoming disengaged and thinking that nothing can be done to change the situation. As a part of your preparation, you’ll want to do a consequence search. What are the consequences of the boss’s behavior? Who is being impacted? Teammates, other departments, customers, you? How? When you find the consequences, you are prepared to talk about the tougher issue.

3. Make sure it’s safe, then talk. Not all times and situations will be equally safe for your boss. Of course, the first goal is to make it safe by mastering your clever stories and getting your motives and emotions right before you open your mouth. When you meet with your boss, if your face is saying that you’ve held court in your head and found him or her guilty before your mouth says anything, the boss will hear the first message. Also, you should consider other factors that create safety. You don’t want an audience. Privacy makes this conversation safer. You will also want to choose a good time. You will know if there are better times—some people are more receptive and have fewer work demands or stresses during certain times of the day or week. And when you talk, start with an observation and question, not a conclusion and emotion. It’s always hard to create scripts in a vacuum, but one that might be helpful is: “I’ve been excited about the new employee involvement program the company has initiated. I’ve noticed a pattern over the past three weeks. Each week, two or three suggestions were given to you and I hear that those have not been passed on to the committee. I’m wondering if we could talk about that. Would that be okay?” In your conversation, you want to honestly and empathically understand the reasons and jointly seek solutions.

4. Know what you’ll do if it doesn’t work. There are a variety of responses you can expect. 1) You and your boss talk about it and find a solution or not—but you are talking and that’s progress. 2) The boss agrees to a solution and then doesn’t change (which leads to another conversation about the pattern and the relationship). 3) The boss gets angry—maybe loudly, maybe quietly. On a bell curve this response is an anomaly and yet many people magnify the tail end to be the middle of the curve. They inflate the small percentage of this happening to a large number and thus choose silence and gossip rather than speaking up. If you play the real odds, you choose speaking up in a safe way. Whatever the reaction, it’s always wise to have some backup plans.

If it doesn’t go well with your boss (it’s not safe, he gets emotional, etc.) there are two possible backup plans you might consider:

a. Share your intentions and excuse yourself. Tell him that you brought up this topic to improve the results and teamwork in the company and that you didn’t intend to cause him any stress. Express thanks for his time and find a way to leave.

b. Suggest a team approach. If appropriate, you might propose that the improvement program can be done by members of the team. After the suggestions are vetted by the team, one team member could take them to the Employee Involvement Committee. This might fit your boss’s preference or style better.

For either of these plans, you need to assess what is happening in the moment and what might be the best next step. The point here is that you’ve anticipated some next steps, so when one option ends, you have a way forward. Preparation and sound anticipation improve confidence.

Speaking up to your boss can be tough. Yet I remind you that if you don’t speak up, you are voting for the status quo. Also, if you gossip or speak up in a frustrated, angry, or judgmental way, you’ve diminished the relationship. Either way, you have become part of the problem. On the other hand, if you can speak up in a safe, considered, and planned way, you are much more likely to solve the problem and build the relationship.

I wish you well,


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3 thoughts on “Speaking Up To The Boss”

  1. Larry

    Good approach described here. One small wording change I would suggest is in point #1 – Frame the challenge in the best possible way.

    Where it says “make sure you come across as curious and helpful rather than frustrated and judgmental” I would change it to be “make sure you are curious and helpful rather than frustrated and judgmental”. The words “come accross” makes me think that your actions don’t need to be genuine.

  2. Carmen

    In addition to this scenario. Let’s say the denying of good opportunities to improve the business continues and the boss still chooses to proceed with certain actions that may not be profitable to the organisation. The reason from the boss may not be intentional but just due to the fact that the boss is simply just not good at managing; although has some excellent qualities in areas of the business. Simple business management standards are not being attended to.
    You do your job and so on and rectify as things come up etc… you then get an opportunity to voice your (and your teams) experiences in this environment along with advising your suggestions for improvement with another above your boss…
    What to do you?
    Do you first meet with your boss….and discuss: “we have discussed these issues before but the pattern continues… and now I just want to tell you that I am going to present this idea, suggestion etc… to so and so…”
    Appreciate your opinion and other comments.
    Thank you.

  3. Dorothy McKinney

    I strongly support talking to your boss, as recommended in the initial answer to this question. I would like to offer an additional avenue for taking your ideas forward, which can be used in either of two cases: (1)after you have tried and failed to have a constructive conversation with your boss; or (2) when your past interactions with your boss have made it totally clear to you that even attempting such a conversation with your boss will make things worse. By the way, I think the only way it can be totally clear that a conversation with your boss will make things worse is if you have tried more than once, using all of the advice given in the initial answer to this question, and discovered that your boss not only is not willing to listen, he also acts worse after each conversation.

    So, what is the additional avenue I am suggesting? In all but the smallest organizations, you can find one or more other parts of the organization (which do not report to your immediate boss) which are also affected by the risks/problems you are trying to resolve, or the opportunities you are trying to take advantage of. You can talk to someone in one of these other parts of the organization, to see if there is a way that this other part of the organization can take advantage of your idea for improvement. If you do this kind of reaching out on a continuing basis, over time you will build up a network of colleagues across the organization who you can partner with to bring improvement ideas to the company.

    Sometimes it can be obvious what other part of the organization to contact. For example, if you are in a design and development organization, and your idea has to do with improving how you buy parts or services from a supplier, you could talk to someone in the part of the organization responsible for purchasing, or supply chain management, or whatever that function is called in your company. If your idea could potentially improve the quality of the products or services your group produces, you could reach out to the part of your company responsible for quality control or testing or customer support.

    If it is not obvious to you what other part of the company might be a potential supporter of your idea, you can use your idea as a reason to get to know more about your company. You can ask people you know for names of others in the company (who don’t work for your boss) who may have insight into how the company operates. Then you can go to each of these people in turn, and talk about the risk, problem or opportunity you see, and ask for their insights. If you ask each of these people you talk to for the names of 2 – 3 other people they think it would be worth your time talking to about this issue, over time you are very likely to discover whether there is anyone in the company you can work with to pursue your idea.

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