Can’t I just hire someone to do sales for me?

This question comes up so often especially from newer business owners – from solo-prenuers to tech startups. The answer in most cases is: not yet.

It seems so logical that you would hire a sales person, as you would an assistant or a bookkeeper.  Unlike an assistant, though, sales are the lifeblood of your business.

building your businessWithout sales, there is no business (the IRS calls a “business” that does not make money a “hobby”).  Last I checked, most of us in business for ourselves are in it to make money; this is our primary source of income.  Many of us are fortunate to love the work we do and receive compensation for it – it’s a beautiful thing.

So, why can’t you hire someone to make sales for you? The main reason is you won’t be successful managing a function you don’t understand yourself.  If you, as the owner, haven’t mastered sales in your own business, you will find it difficult, if not impossible, to properly manage someone in the role.  You will find yourself looking for that person to take the lead, and that person will be looking for you to guide and direct them.  You won’t be able to tell whether the salesperson is making excuses for why sales aren’t coming in or whether the market isn’t responding to your product or service or whether you are missing a big opportunity in the market.

It is in the sales process that we receive valuable insight and feedback from the market.

Prospective buyers tell us their concerns, their wants and needs; it give us real opportunity to design a product or service to meet those needs.  At the very least, we receive information that helps craft our message and position in the market.  We’ve all heard the stories about companies that started with one plan or vision and pivoted based on market feedback – Microsoft, Spot Hero, AirBNB – just to name a few.  Often times, we find our market and niche through being out there in conversation with prospects and hearing what they really want or need.

Is it possible for a good business development person do that?  It can be possible, if that person is a co-founder who truly shares your passion, vision, and mission.  In that case, you may even be willing to listen to them and believe what you are hearing.  Otherwise, you would be receiving the feedback via an intermediary (your salesperson) rather than hearing it directly from the prospect, to whom you could ask questions and maybe even co-craft a solution based on what you know you could create.

When I first started my own business I was told I had to be the best sales person of my service.  Since that time, I have seen it repeatedly in action across hundreds of businesses.  Those who avoid sales or try to hire it out (i.e., try to buy their way out of it), struggle, spend lots of time and money without payoff, and don’t realize the business growth they could.  When you, as the owner of the business, make the decision to truly master the sales process then, and only then, will you be ready to hire someone else for the role.  By that time, you will be confident that you know your market and what they respond to and will be much more likely to be successful managing the salesperson you hire.

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Getting to the Close: Am I talking to the decision maker and how will a decision be made?

Too often in the sales process we find out late in the game that the person we’re talking to is not the ultimate decision maker. We’re speaking to the wrong person, not sure if we’ve addressed the real objections, and don’t know how the purchase decision will be made. In Part 2 of this 3-part series, we focus on how to figure out early who is the actual decision maker, how to speak with that person, and understand how the decision will be made.

This workshop is scheduled for Monday, December 7, 2015 from 11:30 AM to 1:00 PM (CST) in Chicago.  Click below to Register:


  • Learn how to identify the real decision maker, quickly and without alienating your contact
  • Focus your time and effort on the proper person and objections
  • Learn the questions to ask to more clearly understand the decision making criteria, how a decision will be made and the timeline to make a decision
  • Better forecasting of your sales pipeline and prospects
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Every Sale Closes

Each time we have a sales conversation, there is a close. The question is who closes.  Is it the prospect who asks for more time, delaying a decision, or the sales person who moves the prospect to a firm yes or no.  Most people do not want to say no directly, so they delay.  I have to speak to my spouse, or my business partner.  I need to think about it for a week, or a month, or a year.  The timing isn’t right.  How do you know what is a legitimate request and what is a disguised no?

This is one of the topics we will be discussing at my upcoming workshop, A Confused Mind Never Buys – Bringing Clarity and Focus to Your Sales Conversations on Thursday, September 24 from 9am-11am in the IMSA classroom at 1871.

At this workshop, you will learn how to identify objections (hint:  time and money are never the real objections), learn how to ask questions to qualify a prospect, and learn how to identify prospects who are ready to buy.

Tickets are available on Event Brite at:


Call Mary Dombrowski at 773.426.2182 or email

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A Confused Mind Never Buys: Bringing Clarity and Focus to Your Sales Conversations

How many of us start spewing a laundry list of all we can do when asked the question, “What do you do?” Many clients I work provide a wide variety of services and too often confuse themselves as to what is right to offer in any given situation. People seek to categorize and understand. When we list a litany of services or solutions, we immediately present confusion in a prospect’s mind, and a confused mind never buys.  The key is to provide clarity and focus for the prospect, and you do that by asking questions.

We are programmed from an early age to answer a question posed to us. Yet one of the keys to success in sales is to break yourself of the habit and to use that knowledge in your conversations. Asking questions is what allows you to garner the information you need to position yourself and your services as the solution to a prospect’s problem (assuming you do actually have a solution to the problem.)

One client had the opportunity to meet with the management team of a large organization. It was an opportunity to build a long-term and lucrative engagement. There was only one problem. Questions were not asked in advance to understand who is attending the meeting, what their concerns may be, and how a decision to proceed will be made. Instead, my client went into the meeting and talked about all the things his company could do and all the ways they could work together. The meeting ended with no tangible outcomes or next step and my client wondering what went wrong (this was before we started working together).

Asking questions accomplishes two goals. One, you bring specificity and focus to the prospect and to your conversation. Two, you can be creative in designing a solution. When asked what do you do, it’s perfectly acceptable to say something like, “Well that depends. Let me ask you a few questions before I answer that question.” Or, “I help business owners (or whomever). Let’s talk a bit further to help me understand more about your situation and see if there’s a fit.” The prospect will appreciate that you aren’t just seeking to sell something, and that you want to hear in their own words about the challenges being faced. The more information you can gather, the more informed your answer. Their answers, by the way, also give you market feedback allowing you to be ahead of the curve in filling a need.

Some of my favorite discovery questions include:

What would you say is the biggest challenge facing your business right now?

How long have you had that challenge?

What’s stopped you from fixing it in the past?

What has changed that makes you want to fix it now?

How committed are you to resolving the challenge?

What happens if you don’t fix the problem?

Obviously these require some amending to suit your specific service or product offering. The key is to have the prospect speak to the challenge and the pain being caused. Helping bring light to their pain point, and having the prospect articulate it in her own words gives you the information you need to position yourself as the credible solution provider.

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Embracing Sales

A client of mine recently commented that he didn’t want an email going out to be “too salesy.”  Why not?  What is bad about being open with our clients and prospects that we want to sell them products or services they need?  Why hide that we are in business to help their business grow and prosper, and that our business grows and prospers in so doing?

When did sales become such a loaded word?

I have been in business all of my adult life, working up from an administrative assistant to product manager, VP marketing, business owner, and now a sales and business development consultant.  All of my career has been surrounded and often in support of, or in conjunction with, sales people.  Yet it was only in the last 5 years that I made the decision to truly master sales.  Prior to that, sales held no interest for me.  I didn’t want to be in that role. I didn’t think badly of them, and I also see I wasn’t bold enough to put myself on the line as they did.

Then I had an epiphany and realized mastering sales was the ticket to my freedom.  Being in corporate for much of my career, I saw first-hand how little stability there was.  At any moment, you could be let go or close to retirement when your 401K tanked.  It seemed the higher you rose, the larger the target was on your back.  Cynical, I suppose.  But, also true.

I am a firm believer that we all need to treat ourselves as brands, as individual entities and take control of our careers, whether we are currently employed by another or self-employed.  And mastering sales is one way to do that.

Why don’t people master sales?  Fear is big part of it – fear of rejection, fear of ridicule, fear of not being good at it or seeming foolish in front of another, fear of being really good at it and feeling you are manipulating another (you could be, but not if you’re doing sales from a place of service).

Getting good at sales requires you to face your own demons, and conquer them.  There is a personal and professional freedom that comes from mastering sales.  You learn to like yourself.  You learn not to care what other people think (seriously).  And, you learn to actually enjoy helping others achieve their goals by your work together.

Think about it. What’s there to be afraid of?

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