How To Push Back When Your Boss Asks For Something You Know Won’t Work

Nov 10, 2020 | 0 comments

Have you ever tried to raise a concern about something your manager or leadership team proposes? Maybe you have first-hand knowledge that would help to shine a light on the problem with their proposal. If only they would listen!

I think it’s safe to say we have all been there at least once in our career. It’s not an easy position to be in when you realize your experience or ideas conflict with your manager.

In Mean People Suck, I discuss those brave souls who have thrived when they recognize their bosses are wrong and provide practical advice for anyone who is facing the same situation.

Pushing back when you’re not the boss

Whether it’s attempting to adjust a strategy based on your success or working to change the company culture, doing so when you’re not the boss or even a manager within a company can be difficult. However, it is not impossible.

Take the example of Capgemini’s former communications manager, Rena Patel. Rena had two goals: to increase revenue growth for their IT services and to increase the overall awareness of the brand and the reputation of the consultants they worked with, their experts.

But, like many of us in a new job, she was immediately bogged down with requests to do things she didn’t think would work. She executed press releases, tweets, and marketing campaigns while the company’s perception was not necessarily improving and maybe even falling further and further behind its competitors.

The executive team looked at what their competitors such as Deloitte and KMPG were doing – sponsoring major sports tournaments and athletes. They thought sponsoring a professional golfer would be the answer. Everyone in the C-suite was excited, including the chief marketing officer (CMO). Other employees looked forward to the prospect of front row seats at major golf tournaments.

Except Rena knew this would cost the company millions. She did her research and discovered that the company wasn’t just imagining it was falling behind its competitors; it was a reality. Why? The content they were producing was not resonating with their target at all. Further research told Rena that the majority of their audience didn’t even like golf.

That’s when she went to her manager with a proposal. For a fraction of the cost, Rena felt she could create content that delivered on the value by reaching, engaging, even converting the buyers they weren’t already reaching by creating content that their customers wanted.

Rena believed that this effort would deliver sales growth, increase their awareness, and help to build the reputation of their consultants. She was even bold enough to say that her boss could hold her accountable if the project failed.

With the support of both the executives and her team, Rena created a “brand storytelling” program. She set out to answer the real questions on the minds of their buyers. She started tracking the engagement the company received when they published content about topics like Big Data, Cloud, Technology, and all the subjects of Capgemini consulting projects.

And as promised, at the end of one year, Rena had delivered nearly a million new visitors to their website. They saw more than 100,000 new followers to their company page on LinkedIn and were adding 3,000 to 4,000 additional new followers per week. They had 1.8 million shares across LinkedIn in that first year, as well. Better yet, Rena told me that the program generated nearly $1 million in sales in that first year.

Imagine how happy the management team was at Rena’s success.

The art of the pushback

If Rena’s bosses had not been receptive to her ideas, she would have experienced what I like to call the Illusion Point. In short, it means executives continually ask us to do work that we know won’t produce results. Luckily, Rena’s executive listened – in part because she knew how to push back effectively.

The “Illusion Point” occurs when we waste our time, money, and efforts on failed ideas and lost opportunities. We become increasingly frustrated and disengaged. However, a successful push back can disrupt the cycle, so we don’t become part of the actively disengaged employees who are stealing office supplies. But how?

STEP 1: Observe and Learn

Examine the past. How many times have you presented an idea to your manager? What was their response? When you feel that Illusion Point starting to approach, do you go along with your boss’s ideas, or do you challenge them?

More than likely, you’ve accepted that your manager doesn’t care about your input, and you’ve done the tasks he or she asks of you. That may have helped you stay in his or her good graces, but it’s probably also led to unfulfilling work.

Obviously, you don’t want to risk your reputation within your company by stepping too far out of line when you push for your ideas. That fine line can be difficult to gauge, but think about what your boss’s overarching goals have been in the past. How do we strategically challenge our boss without coming across as too pushy or unprofessional?

STEP 2: Ask 3 Simple Questions

Challenging your boss isn’t easy. However, there’s an easy formula you can follow to challenge your managers and get the most out of your meeting with them. It’s about knowing the right questions to ask.

Question 1: Why does this matter?

First and foremost, a leader should be able to explain why an idea or project matters to the company and its customers. By forcing your boss to explain their thinking, it may help them get more explicit on the reasoning behind their decision and how they anticipate it impacting your organization and customers.

How will you know when it’s time to push back? If your boss replies with vague answers such as “Because I said so” or “Because our VP said it’s important,” it’s time to push back.

Question 2: What’s the impact?

Defining the impact of a new initiative means you are ultimately keeping the customer at the forefront. It shows you’re aware you need to be tuned in to how new ideas may change the customer experience. It shows that, even if your manager is excited about an idea, it’s still an issue if it won’t work for the customer. This question brings the customer back into the conversation.

Additionally, knowing the anticipated impact means you are clear on what is expected of you as you execute the idea. It will also illuminate if there is a disconnect between what your manager wants and how you think the customer may react, this question is a good starting point to resolve the conflict.

Question 3: How will this be measured?

We all want to be successful. However, to be so requires clarity. Knowing the details of what your manager expects when you’re executing that idea in real time matters. The end goal might be admirable, but what good is executing an idea well without a measuring system to track that success?

As with the other two questions, this one provides an avenue for the all-important dialogue between you and your bosses, which is what these questions are all about. “When you say you want to see a bigger audience tapped into our marketing content, what exactly does that mean?” “How are we going to actually measure those terms?” “Without incorporating a measurement system into your plan, it’s nearly impossible to discuss your project’s success in concrete terms.”

It is okay to question your boss

As popular LinkedIn author and Daily Mail CTO, Oleg Vishnepolsky said, “Loyal people will tell you what you need to hear, not necessarily what you want to hear.” This quote is just as true for employees with their managers as it is for the reverse. By keeping the customers’ best interests at heart, you are showing loyalty to your company. Speak up, but don’t be mean.


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