There is a way to share and offer value without appearing to be “salesly” or pushy. I think it’s important to discover the balance across all communication avenues. In sales, we are walking on a constant tight rope, trying to find the best balance. The goal should always be to offer the most value and support as you possibly can.

As a part of my series about how to be great at closing sales without seeming pushy, obnoxious, or salesy, I had the pleasure of interviewing Holly Jean Jackson.

Holly Jean Jackson helps entrepreneurs and business leaders love their life and business again. With over 12 years of technology and business experience, she helps business leaders get their groove back physically, mentally and emotionally.

She does this through a combined approach of both coaching and consulting, providing practical and actionable results.

Thank you for doing this with us! Before we dig in, our readers would like to learn a bit more about you. Can you tell us the “backstory” about what brought you to this career path?

I started my career in non-profit. I quickly found myself working in the tech space early on. As I climbed the corporate ladder, I discovered that my strengths were strategizing, building relationships, understanding complex systems, translating between tech and business and creating effective communications.

After a few layoffs, I decided I was tired of building other people’s businesses while being so expendable. So, I decided to start my own company.

As a success coach, I work with business owners, entrepreneurs, and executives on how to build, scale, and lead their companies. I work with all my clients across three key areas: health, clarity, and business.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

Last week, I joined a challenge called Rise Up. Rise Up is helping business owners during the pandemic band together and raise funds for charities that support business owners. The challenge allowed us to nominate a charity we believed in. I nominated SCORE. When my entry made it to the top four, I was offered the opportunity to pitch on their behalf.

The pitch for my charity was broadcasted in front of over two thousand people live on Zoom and Facebook. My charity pitch received the most votes!

My key takeaway is that we must put our passion into everything we do. When we do this, it opens doors for us and allows us to have a huge impact. Make sure you are open to and taking every opportunity that crosses your path.

Are you working on any exciting new projects now? How do you think that will help people?

I am working on building a group coaching program or a mastermind for business owners. This will help bring the cost down for individuals who cannot afford private coaching.

I believe in the power of community. I know that in bringing the right mixture of leaders together, great lessons and insights will come to light.

We learn so much from and through each other. Sharing problems, brainstorming solutions, and celebrating success in a community opens us up to creativity. It shows us that there are other models, ideas and ways forward that work.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I am so grateful to have an amazing tribe of supporters in my network. It really does take a village!

One person I am particularly grateful for is my partner, Dean. He has been a constant beacon of hope. Anytime I have a moment of doubt or a setback, he is always reminding me of how much he believes in me. He supports me and he celebrates with me.

One day I lost a major contract. Given that it was a huge portion of my business income, I was distressed and overwhelmed. I shared what happened with Dean. He looked at me and said “That sucks. But listen, I know things will work out. Things always work out for you. You don’t know how to give up. You never truly fail. Now what can I do to help?”

Having someone by your side that has unshakeable belief in yourself when times get rough is a significant asset. It helps you pivot faster, ground yourself and pivot to the next opportunity.

For the benefit of our readers, can you tell us a bit why you are an authority on the topic of sales?

Many of my clients are uncomfortable selling their services because they are new to a sales approach-based business.

I coach people on how to improve their relationship with money. I teach them how to shift their beliefs around money, how to push through limitations they have set for themselves, and how to reframe the sales conversation.

Instead of feeling like you are taking something from your customer….you are simply offering for the customer to go deeper with you. You are offering them a solution to a problem. You are helping relieve pain by solving their problem.

If you know that the product or service you have will help your customers, then not offering it to them would be cruel. This simple yet profound mind shift is powerful. This shift helps people set and achieve bigger stretch goals.

Let’s shift a bit to what is happening today in the broader world. Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the COVID-19 pandemic have understandably heightened a sense of uncertainty and loneliness. From your experience, what are a few ideas that we can use to effectively offer support to our families and loved ones who are feeling anxious? Can you explain?

The best way we can support our families, friends, and customers is by reaching out and connecting. Call your tribe. Ask them how they are doing. Listen. People need to feel heard. They need to know they are not alone.

Offer to help where you can. People like to help each other. It feels good to help and be of service. Reach out to a fellow business owner and ask them how they are doing. Brainstorm with them on solutions to their current troubles. Support them. When you are listening to someone else and supporting them, it will often reduce your own anxiety.

Reconnect with your friends, family and tribe. Share with them what you are grateful for. How much you appreciate each person in your life and why. When we speak and think from a place of gratitude, it shifts our emotional state to a place of peace and calm.

In business, reach out to your customers and ask them what their biggest challenge is today. If you can, solve it, offer your solution. Help them. This might even give you a new idea to serve your client base in the future. Be open to creativity in the storm.

Ok. Thanks for all that. Let’s now jump to the main core of our interview. As you know, nearly any business a person will enter, will involve some form of sales. At the same time, most people have never received any formal education about how to be effective at selling. Why do you think our education system teaches nearly every other arcane subject, but sales, one of the most useful and versatile topics, is totally ignored?

Even after working in education policy and in the higher education system, I am still baffled as to why we do not teach sales in K-12. Perhaps the system is afraid that if they offer all the core skills needed in K-12 that it would reduce the number of applicants for college.

I think that it could be challenging to find teachers willing and able to teach sales. Oftentimes, people feel “dirty” talking about sales. If we taught our children about money and sales at a young age then we can debunk this falsehood before it starts.

This discussion, entitled, “How To Be Great At Sales Without Seeming Salesey”, is making an assumption that seeming salesy or pushy is something to be avoided. Do you agree with this assumption? Whether yes, or no, can you articulate why you feel the way you do?

None of us want to be perceived as “salesly” or pushy because repels people. Anytime we reach out to our social or professional network, we must weigh the pros and cons. Is what I am sharing going to add value to my people? Is it something I believe in?

Any time we recommend another person’s product, we want to ensure it’s something we believe in. That it’s a tested and well supported solution. Otherwise, we lose social capital, credibility and trust.

Now, more than ever, we are constantly bombarded with ads and supposedly free offers that are only used to add you to a list.

There is a way to share and offer value without appearing to be “salesly” or pushy. I think it’s important to discover the balance across all communication avenues. In sales, we are walking on a constant tight rope, trying to find the best balance. The goal should always be to offer the most value and support as you possibly can.

The seven stages of a sales cycle are usually broken down to versions of Prospecting, Preparation, Approach, Presentation, Handling objections, Closing, and Follow-up. Which stage do you feel that you are best at? What is your unique approach, your “secret sauce”, to that particular skill? Can you explain or give a story?

Closing. I LOVE the closing. At this point, you know you want to work with the client. You know you can help them achieve huge wins. You also know all the most common objectives. You prepare stories to bust through each of them. You build rapport, and you paint them a picture of the future.

One of my most recent closing conversations was with a potential client interested in premier business coaching. We discussed his biggest pain points currently in his business. His biggest wins. His vision for the next 30–90 days. From here, I asked several questions to go deeper on the pain points.

  • I asked of the 3 pains you shared, which one is your biggest challenge?
  • What keeps you up at night?
  • How has he tried to fix this problem?
  • What worked and what didn’t?

Taking notes in their words on key things is important. Repeating back to them what you heard is also important because they feel heard and understood.

From here I shared a couple short term actions and quick wins he could take related to the problem. Then I painted a long-term picture for him aligned with what he shared earlier in the interview. I share how in working together, we would put together a step-by-step plan to get him to that goal and beyond.

At this point, I ask him if he wants to hear about my coaching programs. If yes, then I go into detail around the best coaching program for him. I explain that each package is custom. I share the benefits, the bonuses and the price.

Then I ask him if this sounds like something he would like to pursue. If yes, then I ask him when he would like to get started. Locking in a starting date verbally is so key.

Each of these steps is getting micro agreements along the way and building trust. This seals the commitment and the start of an awesome client-coach relationship.

Lead generation, or prospecting, is one of the basic steps of the sales cycle. Obviously, every industry will be different, but can you share some of the fundamental strategies you use to generate good, qualified leads?

I use an intake form when clients schedule a discovery coaching call. This helps me determine if the problems they are facing are ones I can help with. I don’t want to waste their time. It also tests whether the potential client is coachable.

If they don’t show up to the appointment or are late, this is also a red flag. I don’t want to commit to helping someone who can’t respect my time. I also only want clients who are ready to take action so that they can achieve big wins…….clients who are ready for transformation.

With my referral partners, I keep in close contact, so they are clear on who is a great referral for me right now. Your ideal client may change over time. Keep in touch with your partners so they can pivot with you.

In my experience, I think the final stages of Handling Objections, Closing, and Follow-up, are the most difficult parts for many people. Why do you think ‘Handling Objections’ is so hard for people? What would you recommend for one to do, to be better at ‘Handling Objections’?

The first most critical step is to KNOW what your ideal client’s most common objections are. Once you know what they are, develop client stories that address each objection. Make sure you know each story in your sleep. Be prepared to use them when you need to.

Address objections before they come up. In the closing call or on the sales funnel page, have a bonus or a story that addresses every commonly held objection your ideal client has.

Make sure you are expressing the problems you are solving in the words of your customer. Explain how your service or product will help them bust through them.

Check in with yourself to ensure that you don’t personally have the same objection. For example, if you think your product is priced high, I promise you will get the “it costs too much” objection every time. Oftentimes, the objections reflected to us from our customers are due to beliefs we need to fix ourselves.

‘Closing’ is of course the proverbial Holy Grail. Can you suggest 5 things one can do to successfully close a sale without being perceived as pushy? If you can, please share a story or example, ideally from your experience, for each.

  1. Explain the problem very clearly in the words of your customer and then expand upon how painful it will be if they do not solve it today.
  2. Example: “Sally it sounds like you are having a problem with getting clients right now; in particular, the right clients for your services. If you don’t figure out a solution to that problem very soon, you will be even more financially strained, working even longer hours trying to fix it, and feeling discouraged.”
  3. Share client success stories that show big wins and break free from the problem expressed.
  4. Example: “Sally, one of the most common challenges my clients face is attracting the right clients. When working with another client, we went deeper into his client avatar. He interviewed ideal clients and discovered where those people hung out. What kept them up at night and the more he explored this, the more he narrowed his niche and his ideal customer. Once he did this, it streamlined all his marketing. It fixed his story. He was able to describe more clearly the problems he solved for his clients, and he immediately began attracting the right clients after updating his materials to reflect this. His business is extremely successful today.”
  5. Offer bonuses or stories that solve for any potential common objections.
  6. Example: “Sally one of the biggest concerns my clients have is making the investment into coaching. A lot of the investment is more about the client. The investment helps you show up in a different way. It up levels your commitment. If you’re wondering why your competitor next door is doing so well, it’s likely that they have hired a coach to keep them on track and share fresh ideas and new perspectives. In the end, the investment is small when it helps you stay ahead of your competitors and it saves you time.”
  7. Listen carefully and relay back to your customer what you are hearing in their words.
  8. Example: “Sally, I am hearing that you are frustrated with business development and that you are tired of attracting the wrong customers. Did I get that right?”
  9. Ask them if they would like to hear about your product or service after doing steps 1–4 and building constant rapport.
  10. Example: “Sally, I feel confident I can help you with your problem and I think we would work very well together. Would you like to hear more about my coaching packages?”

Finally, what are your thoughts about ‘Follow up’? Many businesses get leads who might be interested but things never seem too close. What are some good tips for a business leader to successfully follow up and bring things to a conclusion, without appearing overly pushy or overeager?

Make sure you add your potential clients or leads into your CRM (customer relationship management system). I like to keep in touch with them every 2–4 weeks. I send personal “checking in” emails. Sometimes I share a free webinar or resource I have that could help them.

It’s important to keep the relationship going. Make sure the follow up is engaging and personal. The more you get a response, the better you are doing. Engagement is key.

Think long-term. Sometimes it’s not the right time for a potential client to work with you. Sometimes it just takes that long to build the right amount of trust before they buy from you. I have had customers where the pipeline was as long as 18 months. It happens, so keep at it. Keep your pipeline relationships healthy and engaged.

As you know there are so many modes of communication today. For example, In-person, phone calls, video calls, emails, and text messages. In your opinion, which of these communication methods should be avoided when attempting to close a sale or follow up? Which are the best ones? Can you explain or give a story?

If the sale is a large ticket item, I recommend a video call or an in-person meeting. It is easier to build rapport and trust in person or face to face. This is also why I like to sell from stages. In a 30–60-minute workshop or keynote, you have built social credibility, trust, and shared testimonials. It is much easier to sell in that environment.

For follow up, I like to schedule a follow up call if the lead is on the fence and wants to think about it. I don’t want to exert pressure. I offer to follow up and answer any questions they have and lock in a date and time to do so. If not, I follow up in email.

For my potential clients whom the timing isn’t right, I also occasionally text them with helpful resources or to check in.

Ok, we are nearly done. Here is our final “meaty” question. You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

My long-term vision is to create a non-profit to help kids between 13 and 16 boost their confidence through empowering speakers, teaching soft skills, and providing support. I want to partner with the education system, community leaders, and other non-profits to make it happen.

I know there’s a tremendous burden on our education system. I think having new groups to supplement and support education is a better approach.

The movement I want to create is empowering our children to think big. Dream big and to gain an entrepreneurial spirit at a young age. They are our future so let’s invest more in them.

How can our readers follow you online?

Feel free to check out my website and follow my blog at www.HollyJeanJackson.com. Or follow me on Instagram https://www.instagram.com/coachhollyjeanjackson/, Facebook https://www.facebook.com/hollyjeanjackson/, or LinkedIn https://www.linkedin.com/in/hollyjjackson/

I would love to hear how things are going in your business and career. I hope you start closing more deals. And feeling less salesly in doing so!

Thank you for the interview. We wish you only continued success!


Holly Jean Jackson: “How To Be Great At Sales Without Seeming Salesey” was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.