Are You Too Nice to Succeed in Business?

“You’re too nice.”

These three words have haunted me for as long as I can remember, from my first professional performance review to my first days as a manager at a public company and even today when fellow entrepreneurs try to give me helpful advice.

My mentors, peers, and friends are all correct in their assessment of me – that I am, most definitely, too nice. I have a tendency to over-deliver and take calls at 11PM when realistically, I should do neither.

If I were less nice, I’d have an easier time as an entrepreneur and be more successful. That’s the explicit or implied advice I’ve been getting.

But “cutthroat” isn’t me. Yes – as an entrepreneur, I need to be competitive, and I am. I enjoy pushing myself to new heights, challenging my limits,  and pursuing aggressive milestones. Last November, I challenged myself to quit my day job and pursue my growing side-business full time. Now, I’m pushing myself to scale my efforts and achieve steady, sustainable growth.

But when it comes to reducing how nice I am, I’ve refused to do that. The good news—one of the milestones that I am most proud of is that I’ve learned how to reposition what some people consider my biggest personal weakness – my niceness – into my biggest business strength. Here’s what I mean:

1. The nice way to eliminate your competitors

I know several entrepreneurs who refuse to reach out and build relationships with their competitors. They worry that others will steal their secrets or move in on their clients. People like that think I’m crazy for building close friendships with many founders and consultants who do exactly what I do – create educational content for B2B software companies. It may sound weird, but I firmly believe that these individuals are my strongest allies. We are one another’s eyes and ears into the marketplace. We’ve even joined forces to team up on projects. Two of us are even working on a book together.

This year alone, this ‘ecosystem’ has generated a mid five-figure revenue stream to me (and them).

I care about the success of my so-called ‘competitors’ tremendously. I respect their work, enjoy learning from them, and could never imagine ostracizing them. It makes more (business) sense to keep them close and to support their growth – so that our businesses evolve together. My revenue stream proves that our target market can support – and fully embrace – us all.

2. Free marketing

I regularly work 14-hour-days on my business, which stretches me pretty thin, but because I’m too nice, I always manage to squeeze in time to help people. I am always willing to take a meeting (or phone call), join a late night brainstorming session, or provide advice to my fellow solopreneurs. My biggest wish is that there were more hours in the day for me to accommodate everybody. I’ve actually scheduled “office hours” to accommodate demand for my time, and unfortunately, these book out weeks in advance.

I’ve been advised to raise my rates or charge money for my “free” consulting time. I’ve thought about it but can’t bring myself to do it. If someone – even a complete stranger – needs something from me, I’m more than happy to be a resource.

And believe it or not, my “free” consulting time has been a driver for my business. Some of these ‘random connections’ have become long-term paying clients. Others have become steady sources of referrals and introductions. I’ve also landed teaching and speaking gigs from helping people.

I have never spent a dime on marketing or advertising my business. Instead, I focus on maximizing my opportunities to add value – even during unbilled consulting sessions.  The referral ecosystem is my engine, and my ‘niceness’ is my fuel.

3. The anti-sales

In 2012, I interviewed for a sales role at an up-and-coming Bay Area startup. Part of the process involved an analysis of how I’d handle a negotiation situation. After saying what I wanted to say, I asked for feedback. The company’s response?

“You did great, but you could have pressed the customer much harder by doubling the hypothetical commitment.”

I ended up getting the job, but I felt super uncomfortable with this philosophy. The fact is that I don’t like selling unless I’m offering my customer a clear ROI on what they’re spending. Any other “hard” sell feels awkward.

I came to the conclusion that I am absolutely, 100% the opposite of a sales machine.

But when I started my business, I realized that I was exactly that – a sales machine. I’ve generated more than $500K in sales without feeling like I’m selling. My secret is no secret – it’s the fact that I genuinely care about providing value and helping my customers grow.  And if they don’t want to do business with my company? That’s fine too. I completely understand company revenues ebb and flow, and at the end of the day, it’s the macro-level metric that counts.

I have all my customers sign contracts, but only 5% of my revenue comes from retainers. Even those customers, if they want, can fire me on the spot. I’ve been told that retainers are an absolute must in my industry (and by not forcing people to accept a double-digit retainer, I am essentially, making the stupidest decision on earth), but I’ve decided to ignore this advice because I feel good about giving my clients flexibility. The result has been double-digit month over month growth.

Rather than talking about money, we focus on solutions and projects that we can tackle together. We focus on the ROI of each specific initiative to ensure that my customers are deriving value from what my company provides.

The blunt truth is that the freelance model is not for the weak of heart. I am constantly dealing with moments of uncertainty, which make me feel immensely stressful. My clients could fire me and I would have zero recourse or protection. But the key to driving growth for my business, however, has been to embrace — rather than react — to this uncertainty with strict retainers.

Despite moments of frustration and uncertainty, it’s empathy that keeps my business going — and growing.

4. Thinking with my head

I take pride in being a kind, genuine person — but I’m not naive. People try to take advantage of me. People overstep their boundaries and have even cursed at me.

I’m nice, but I’ll never be a doormat.

A fellow entrepreneur once told me that I should  — logically — define a line that I will never let clients (or anyone else) cross. I defined this line and when someone crosses it, I cut them from my life and business — permanently.

This process has taken significant patience and practice, but it’s been invaluable to keeping my ‘niceness’ — my best and worst strength — from getting the best of me.

But I’m not always ready to cut the cord.

I work with people who are constantly under pressure — the stakes are often high, especially for entrepreneurs who put their entire lives on the line. When somebody frustrates me, I ask myself:

1. Does our relationship, mutually, continue to create business value?

2. Is the business relationship an opportunity cost for better and brighter opportunities?

3. What, personally, could be inciting this behavior?

People are complex, and even the most kind-hearted sometimes act in frustrating ways. I deal with these situations by focusing heavily on the long term.

Your thoughts

What has been your biggest weakness in business? How have you re-positioned this “disadvantage” into a growth driver for your organization? Share your thoughts in the comments section below. We’d love to learn more and for you to continue the dialogue.

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