Powerful Insights 

Articles, interviews, inspiration, and tools to help you balance your power with purpose

Powerful Insights 

Articles, interviews, inspiration, and tools to help you balance your power with purpose

How people pleasing is killing your business strategy

business strategy corporate negotiation small business Aug 18, 2022
Joanne is smiling and holding a white sign with black text that reads:

People-pleasing is hands-down THE most common negotiation blind spot that I observe in my clients. And in most cases, that behaviour is a significant strain on their business. It affects their personal experience as a business owner (and never in a good way). But it also affects their profits. If you are a people-pleaser and trying to niche or differentiate your business, you are in for an exhausting ride.

Every time you negotiate – even if it’s only a negotiation with yourself – it’s critical that you know which blind spots are most likely to sabotage your success. Understanding the steps of negotiation is great, but if you don’t understand your own emotional process in a negotiation, then you risk your profits, your partnerships, and your potential. The Women’s Entrepreneurship Knowledge Hub does an annual review of women’s entrepreneurship in Canada…and every year, they point out that a lack of negotiation skills are holding female entrepreneurs back from success.

A blind spot is a behaviour that a woman exhibits without even realizing it, which limits the effectiveness of her negotiations. Last week, I talked about the impact of Generosity (blind spot #1) on your business strategy. This week, I want to dive into the implications of people-pleasing on both Focus and Differentiation strategies.

People-pleasing limits your chances of running a successful business

The practice of being a people-pleaser is a never-ending hamster wheel of fear. Fear of failure as a business owner or entrepreneur. Fear of relationships breakdown. Fear of reputation loss in your industry and professional network. Fear of being accused of not being enough.

If this is something you struggle with in other areas of your life, you can bet it will probably be a blind spot in your business. The problem: it is an unrelenting blind spot. Not only do you respond to every little request with a chipper enthusiasm. But you also anticipate those requests in your own mind. You think about other benefits or ways to serve your clients. And when you’re a super-hardcore people-pleaser, you actually deliver on those things. Under-promise and over-deliver is your mantra.

It might seem like it will help; it won’t.

From the outside, this might seem like a strategic approach to doing business. People have wants and needs. You’re pretty damn good at anticipating and meeting those needs. They pay you for doing that. You need money. Match made in heaven, right?


When you are constantly going above and beyond, you are creating an unrealistic set of expectations that no other business owner would be able to keep up with. Worse, it’s a model that is all but guaranteed to burn you out.

People-pleasing puts you at a disadvantage in business growth and sustainability

When you are focused not only on what you do well, but also on providing whatever the other person wants, you actually end up doing them a disservice. That’s because, as amazing as I know you are, you can’t be stellar at everything. So when you’re trying to do everything, you naturally downgrade the quality of all of your contributions…even the ones where you are the most qualified and capable provider.

We all have a zone of genius – a set of skills and talents that are unique to us and which we actually really love using to benefit others. For me, that’s helping others be strategic in their businesses and their negotiations. The problem is that there are a ton of other skills and talents that we can deliver on, but which really don’t optimize our time.

When you’re a business owner, your time is everything. You are the brains of the operation. The strategy, the decisions – these are things you are never going to contract out. And yet, we put them on the back burner so we can deliver on wishes and whims of clients, even when those wishes and whims don’t align to our business plans and strategies.

People-Pleasing limits your ability to build and follow a strategic business plan

As I talked about last week, differentiation strategies are about delivering something that can’t really be compared. If you have ever tried to purchase house insurance, you may have a sense of what I mean. Trying to compare policies is nearly impossible, because each insurance company offers a unique combination of benefits and coverage, and all with different, non-comparable price points.

This is a useful strategy for entrepreneurs who have identified a need that can be filled in a unique way, which is difficult for your competitors to replicate or replace. In the service industry, differentiation is a great choice. Let’s take two coaches, for example. They both might offer one on one sessions, but with unique outcomes guaranteed within their packages. Ultimately, they are trading time for money. But the more distinctly they can define their approach and their outcomes, the harder it is to compare among coaches. Sure, as a consumer, you can do the math on their hourly rate. However, because they are each incorporating a different background and intellectual profile, taking 12 hours with one coach wouldn’t necessarily lead you to the same outcomes as 12 hours with a different coach.

The pain of people-pleasing

Now if you employ a differentiation strategy AND you are susceptible to people-pleasing behaviours, you are going to struggle to keep your business distinct. If you bend to every whim of every client and adjust your programming or product so that it can be directly compared to another business, then you start to enter the dangerous territory of cost competition.

You do not want to start a price war in your industry. The only person it benefits is the client, and it can do long term damage to the perceived value of the products and services you sell. There is a reason that Chanel bags never go on sale. If they ever did, they would create an expectation of regular sales. Instead of purchasing at full price, everyone would just wait them out, which would destroy the company’s profitability and decrease its perceived value. 

People-Pleasing and Focus Strategies

Focus strategies are all about niching down to a very specific target audience. My business uses a niche strategy, and is built on the knowledge that there are no other negotiation training programs designed around the specific needs of women entrepreneurs.

As I’ve shared before, I do still struggle with a bit of people-pleasing now and then. It comes out when I decide to write an article or build a small program designed for a client who isn’t a female entrepreneur. You might question my wisdom to avoid that kind of branching out. There are clients in different sectors who need help with negotiation. I like money. Why not serve them all?

In fact, funny story – early in my business’ life, my husband and I had a conversation about the profitability of my company. He asked, completely without prejudice, why I wasn’t targeting men in my programming. In his mind, I should have been going after the sure thing – the target that was already advancing in their careers, and who were already buying negotiation support from strategic advisors.

As I explained to him, I’d rather be in a niche where there are no direct competitors. I can have the loudest voice. I can shape the narrative. And I can have the biggest market share – instead of fighting for scraps with business and strategy negotiation coaches who serve the same audience.

Perhaps the biggest benefit is that I only have to speak to one type of client. That means I need to do less than half the marketing work to draw in people who work for companies and people who own companies. My website can be clearer. My message focused for women in business. Nobody is confused. 

People-pleasing in action

When we adopt people-pleasing behaviours, we only make things harder for ourselves. Whether we create distractions, diffuse our impact, or adjust our offerings so that our incomparable businesses become comparable, there is no good that comes from falling into the people-pleasing trap.

You’re at risk of making poor decisions if you find yourself thinking one of the following:

  • I wonder what else I can do to make this client happy
  • If I don’t overdeliver, the client will be unhappy
  • I’m worried the client may not like/respect/want to work with me if I don’t…

Five questions to ask yourself for negotiation success

Before you jump in and offer them the world, pause and take a breath. Ask yourself these five questions for negotiation success:

  • What is the minimum offer I can make that will meet their needs?
  • What is the legitimate risk of not overdelivering?
  • Will they actually be unhappy with me or is this all in my own mind?
  • What do I risk if I give in to my people-pleasing desires?
  • Am I willing to risk those implication

Try these questions out the next time you’re tempted to go above and beyond, and let me know how they help to shift your thinking.

Identify your negotiation blind spots for business success

Did you know that 60% of women never negotiate? This leads to missed profits and opportunities to grow business. My Essential Skills for Entrepreneurs course will change your relationship with negotiation and help you become a better negotiator. If Negotiation makes you uncomfortable, insecure, anxious, afraid, or any other stomach-churning adjective (hello, people pleaser!) this course is for you.




Want powerful advice in your inbox?

Sign up for my latest articles, tools, and offers - delivered with personal insights and cheeky perspectives.