Guest post by Ashley Preston

I know you want me to write a simple how-to manual for lead generation right now – something that helps you lay out your plan in a neat, step-by-step fashion. However, I am here to tell you that it does not exist.

There are no one-size-fits-all solutions to closing sales because no business offering is the same. Anyone who tells you otherwise is not showing your company’s unique value the respect it deserves.

Creating more leads and converting them into sales is both an art and a science, so we must have the mindset of a mad genius such as Salvador Dali, in addition to the painstaking laboratory rigor of Marie Curie. It takes an artist’s view of layers, tone, color, experimentation, proactive and reactive adjustments, and a little bit of bravery to find out what works for you and your business.

Think Like an Artist Instead of a CEO

As an artist, I can tell you that there are plenty of times I have started a drawing, spent hours on it, stepped back, and realized something was still not quite right. When that happens, I am left with two options.

Depending on the issue and the medium I am working in, I can sometimes correct it and keep moving forward with that piece. Other times, though, I see that I will ultimately spend less time working by abandoning that version and starting from scratch.

In sales, sometimes we spend so much time in the rapport-building process that we lose sight of what we’re trying to achieve – a sale. It may be beneficial to step back from the sales process and consider what nuance or elements have been missing. Are you lacking the warmth of trust, the heat of authority, or maybe the cool shades of thoughtfulness. Treat the relationship like a creative collaboration, adding these new tones as needed.

You may also want to look at your social media channels and the message they are sending about you and your business. What types of posts are getting the most interaction from your audience? What is getting them to comment? Are they responding more to questions or product information or funny posts? What content is getting the feedback you’d hoped for? Adjust your content strategy as needed until you’re attracting the right attention to your business. 

Pay close attention to the flow of your sales conversations. You may even record them and analyze the play-by-play. Pay attention to the language your customers are using when they are interacting with you. You can mirror those word choices to better connect with them. Pay attention to their complaints if they have them; they are sharing pain points you might be able to help resolve. Conversations can reveal so much when we allow ourselves to let the moment dictate our actions.

I will sometimes start a painting with little idea of what I want to create – letting the painting naturally materialize through experimentation. This is much like analyzing client needs – taking one step (and one question) at a time until that discovery process is complete and a richly detailed image of the client's problem has taken shape.

While I have been immersed in art since I was young, there are plenty of techniques and styles I have not touched upon yet. I will often pull out my old art tutorial books or watch a YouTube video to see how other artists tackled something, but even then, it is up to me to incorporate the information in a way that works with my own style.

You may consider watching YouTube videos by thought leaders and sales experts (Jill Konrath, Gary Vee, etc.) or watching some sales role-play videos to tighten up your practice.
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As an artist, you need to be willing to make mistakes and adjustments. The process of creating is just as important as the result. Allow yourself space to let the process tell you what it needs. Give yourself permission to start over when it is called for and don’t waste time on something that no longer works.

Give Yourself Space to Experiment

Bravery is not the lack of fear – it is action despite that fear. It is terrifying to take risks. Even as someone who is comfortable with some risk, I still feel afraid when I take chances, even if I believe the odds are in my favor that things will be fine. 

Often, successful people are willing to deal with short-term discomfort because they know there is no perfect approach. All knowledge is useful. Learning from your sales and messaging mistakes allows you to refine the messages that best land with your ideal clients.

Sales is not a numbers game. It has always been about quality.

Make time to experiment with new ideas. Each week, or each workday, testing out new concepts and playing with sales pitches can make a difference in the results you’re getting. Think of all the things you might experiment with -- your greeting, your signature, your subject line, the first sentence, the length of your message, the tone of your message, or the font you’re using.

It takes conscious effort to allow yourself to openly create, but the rewards you reap from that kind of healthy risk are tangible.

Use Data to Refine Sales Messages and Get Results

There is not much point in doing something if we are unwilling to learn from it. The beauty of that type of experimentation is that you can collect a wide range of direct data to help you refine or recreate your message.

Pay attention to what techniques and language are connecting (or not connecting) with clients. Maybe they are smiling or leaning forward when you use a certain phrase, or you notice that you have connected with numerous potential clients through a certain social media platform. You may leave a sales meeting feeling how much they love you, but then they go radio silent and stop responding to your calls. Use that information to tweak and refine your strategy.

Keep a list of pitches that have worked well. Take note when someone responds exceptionally to something you said. Track response times to see when potential clients are generally online. Track your follow up and the time it takes to get a response during the week compared to over the weekend. Use whatever information you can pull to test your experiments, and adjust your strategy as needed.

Stop Looking for The Perfect Sales Conversion Process

Just stop. It can feel lonely and stressful when making choices that affect your business, reputation, and even income.

However, it is important to remember that you did not come this far to only come this far. You have made difficult choices before, and you will continue to make choices that you think will best benefit your business.

And that is the whole point. Whether you are the Director of Development or the CEO, you likely want to be in charge and have some say over what happens to the clients in your pipeline. You know what is best for your clients and your business, so own it. 

Be Comfortable with the Unknown

It takes effort and practice to have faith in your process. We often want immediate results and concrete proof that something will work before we even attempt it, but you will get much farther by trying new ideas, using first-hand data to pivot your message and approach, taking the reins of your business and doing away with the limitations of any out-of-the-box program or process.

It’s our mission to identify development opportunities and help our clients think like artists. The best artists are willing to shape, and even scrap, their own work. Find your power, formulate your plan of attack and throw away that dusty old playbook. If you need help getting clear on your next best steps or want to schedule a conversation, send us a message.

Guest post by Ashley Preston

You did it. You finally took a chance and hired a coach to help you. They are promising to help you turn your life and your business around, but as you work with them, you can’t help feeling like something is a bit off.

Are you having buyer’s remorse? Or is it something else? Are you comfortable talking to them? Are they making it easy for you to open up and share what you need to with them? Or do you find yourself hesitating to use the services you paid for?

If you’re having doubts, you might want to ask yourself if you’ve hired the right coach. Here are five signs it might be time to look for the exit.

1. They Bully You or Harshly Judge You

You hired a coach because they could help you in areas where you admitted you’re struggling. They are there to encourage you; not make you feel guilty or dumb for not knowing something in the first place. No one should make you feel inferior for owning up to your own shortcomings and getting help to improve those personal limitations. That’s how we learn and grow as people.

If your coach is making you feel like you’re inferior, if they are talking down to you, or dismissing your concerns without valid reason, you’re not dealing with the kind of person who should be working as a coach. You can’t solve your real problems when you can’t talk about them without fear, and you can’t be truly vulnerable with someone who doesn’t show you the respect you deserve.

2. They Minimize Your Experience, Education, or Training

Coaching takes a great deal of compassion, empathy, and patience. It requires the coach to step into your shoes and understand where you’re coming from. A good coach will point out your strengths and remind you how far you’ve already come. That coach would embolden you to use whatever tools are at your disposal in order to move forward with confidence while helping you sharpen up other areas in your life so you can be even more effective.

However, if you have a coach who is telling you that because your training or experience didn’t come from the “right” place, or it’s not valid, then you have a crappy coach. It doesn’t matter how you learned what you know. As long as you have your facts straight and are confident in your experience, your perspective is valid and your knowledge is valuable. Don’t let anyone tell you otherwise, especially the coach who was hired to highlight what you bring to the table. No one gets to dim your shine!

3. They Tell You What Kind of CEO You Should Be

Did you build a business? Did you make decisions and sacrifices to get where you are? Did you create something and see its success bloom? With all that experience, you have developed your own style of work and management.

While coaches can help you reflect on parts that might not be working, or help you see some fresh perspectives that you haven’t considered, it is not your coach’s job to change everything. Why fix something that isn’t really broken? Don’t trust a coach who can’t see your leadership potential and success.

A good coach will work with you to create a better mindset so you can be the best version of yourself, not tear you down and rebuild you from the ground up. Walk away from the coach who makes you feel like a terrible CEO when it’s clear that most of what you’re doing worked long before they walked into the picture.

4. They Tell You They Know Exactly How to Fix Your Business

One size doesn’t fit all. Some coaches want to believe that a one-size-fits-all approach will work, but it is simply a lazy approach that doesn’t take into account the complexities of your operation or the free market. While a good coach can provide feedback, structure, and advice, these things should act as guidelines. You should have the room to ultimately make decisions that fit your own business without feeling guilty or stupid for doing so.

If your coach is saying things like “just trust the program, it works for everyone” there’s a good chance that their system isn’t battle-tested, and they don’t understand the importance of giving you the power to make the choices that will ultimately serve your company best. Only you will know what that is, and a good coach will know when to encourage you to do so.

5. They Bombard You With Too Much Information

You need to walk before you can run. A coach is there to develop your potential. A good coach wants to facilitate the learning process by challenging your thoughts and creating an environment that enables you to take it all in. They know that you should master the fundamentals before moving on to more advanced routines.

Good coaches care about how much you get out of the program. A bad coach, however, will likely throw a massive amount of information at you, sometimes in no particular order. They do so because oftentimes it makes them feel smart, and if you can’t take it all in, then it’s not their fault that you don’t succeed. It is a lazy approach that leaves you wanting.

If your coach isn’t taking the time to explain things, and if they aren’t giving you information that is digestible, you’re not going to benefit from the program like you should.

There Are Too Many Coaches Out There. Don’t Settle for Bad Coaching.

You should get what you paid for. You should feel supported and seen by a coach. You should feel like they are there to help you. You should feel like they are learning from you as much as you’re learning from them. You should be able to trust them and their vision for you. 

If you don’t feel that way about your current coach, then it’s time to make a change. Don’t settle for less than what you deserve. Contact the team at Illustrious, ask about our Amplified Executive Coaching program, and let’s get you back on track with someone in your corner who believes in you.

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​Great leaders hire great coaches. 

Over the last 7 years, I have had the honor and privilege to coach some of the most gifted, passionate and powerful business leaders — from other coaches to small business owners to Chief Innovation Officers.

Coaches don’t need to understand their clients or the business, they need to believe in them. They need to see the utmost potential in their client and identify the growth and development opportunities for that executive to leverage.

People hire coaches for a reason. 

Some of my clients were at a crossroads, overwhelmed by uncertainty while trying to navigate their business at the length of a flashlight beam in the darkness. 

Some of them were stuck — immobilized with fear and overwhelm because of financial pressure or because they were comparing themselves to others. 

Some were growing so fast that they were sickened by their own velocity. 

Some were bobbing in uncharted waters, depressed, isolated, and needing physical contact or someone to talk to.

Some had found success and simply wanted to find ways to give back to their community or show up as a better leader.

In every case, we talked about it. I asked questions. I noticed where topics were avoided, or where their body language shifted, or where they simply lacked the belief in their own power and agency. And then, I asked a different question.

Each time, they came away with some kind of insight and commitment to change -- one massive action (or small, next, best step) that they could take toward growing their business or becoming the visionary leader that they were meant to be.

Here are the top 8 areas in which I’ve seen clients move the needle, with sometimes game-changing breakthroughs.

1. SELF CARE

An insight into self-care may be as simple as “I need to have more fun!” Other times, the client has realized “I need to take care of myself otherwise I can't help anyone else.” I’ve also heard clients say, “I’m the one creating all of this pressure on myself.” This is important because they have realized it is their own hand on the levers and gauges creating the tension and conflict within not only themselves but their relationships. 

One client, who had been quarantined during the pandemic, was so affected by the isolation that she couldn’t focus on her business at all. I could see in her downcast eyes and her buckled shoulders that she was sad. I could hear in her voice (esophageal constriction and vocal fry) that she was weak. 

By the end of the call we had identified a new, very specific, goal: “I am starved for touch so this week I will schedule a coffee with my friend and hug them for at least 20 seconds.”

*Coaches are not therapists. We don’t look back at wounding, we look forward and focus on goals. If a client displays symptoms of depression it is our responsibility to refer them to (or encourage them to seek out) a clinical approach.

2. MINDSET

Sometimes clients forget how amazing they are. They forget everything they’ve accomplished or only remember the last thing they did (the play before the timer ran out, the last speech of the campaign). Imposter syndrome can creep in and their mindset may move from a dynamic, growth state to rigid and fixed.  

By reminding clients how amazing they are, and inspiring them to affirm their attributes or accomplishments aloud (sometimes very loud), they can turn that mindset around. I’ve heard things like, “Wow! I’ve done some amazing things in my life and I need to remind myself what a badass I am.”

One client, who doubted their worthiness, pushed back on her own negative self-talk saying, “No. I deserve to make good money. I want to share my business and my mission with the world. In order to make that happen, I need a bigger platform. So I need to keep suiting up and showing up.”

3. PERFECTIONISM / FEAR

Resistance feeds on fear. 

Recovering perfectionists will tell you they deal with a chronic and crippling fear of failure and disappointing others -- that they simply cannot launch version 1.0 because it won’t be good enough. They may say they have “high standards” and that their superpowers lie in “planning” and “thinking things through.” The coaching goal is not to make the client smarter, but more effective. And that requires thinking and action.

I like using the analogy of the sea and the stars. The sky represents perfection. We can gaze upon it from afar, appreciating the beauty of our sunsets or the splendor of the Milky Way. We can use the North Star to guide us and chart a clear course. The waters we’re on, however, are choppy -- tossing us back and forth, threatening to swallow us whole. The boat we’re sailing is constantly being rebuilt and repaired. Life (and your experience or interpretation of it) is imperfect. Don’t confuse the water with the stars.

The best you can hear from a client is that “expecting perfection is unrealistic and unfair to myself and others.”

4. TIME MANAGEMENT / STRATEGY

The brain is not designed to hold all of your appointments and deadlines. It is not intended to retain your annual strategic plan or your team’s objectives and key results. That's what mark-making and visual tools are for. Write that shit down.

The most surprising and staggering observation from my years of coaching is the amount of business owners and executives who don’t have a handle on their schedule or their plan.

Some are wasting time where they shouldn’t. (“If you’re saying yes to this, what are you saying no to?”) Some don’t use a calendar or they use too many. Some use a calendar for their business, but not for their family, leaving their spouse and children feeling stranded, angry, and confused.  

When we break the big thing into smaller things, I’ve heard clients say, “That doesn’t feel intimidating. My brain can handle it when it’s broken down into smaller chunks.” 

For small business owners, this is vitally important. I’ve heard them say things like “I need to create a visual sales pipeline to track my leads so that opportunities stop falling through the cracks.”

When it comes to time management, I do a happy dance every time I hear a client say, “I will buy a planner and start writing down my commitments” or “I will look at my Google Calendar every morning so that I feel like I am more in control of my day.”

5. STORY

It’s important that my clients know what story they’re telling. I do a lot of StoryBrand workshops, helping organizations put their client in the center of the story, elevating their customer as the hero, and showing up as their guide. We talk about the work of mythologist Joseph Campbell and novelist Kurt Vonnegut. We talk about The Hero’s Journey and the shapes of stories.

When coaching clients consider the beginning and middle of their story from the outside, it’s sometimes easier to imagine where the ending should logically take them.

I’ve heard clients have major insights such as, “Oh. I’m not the Hero at all. I’m the Oracle.”

I’ve also heard them say, “I’m further along in my journey than I thought I was” and “All the ingredients of hope and change are in my story. I just need to get better at telling it.”

One client decided to tap into her own history as a survivor of abuse in order to help others tell their story and grant them the power of choice. She said, “So many people feel like they don’t have a choice. If I can create choice for others in restricted spaces, there is unlimited potential.”

6. MARKETING / SALES

From writing polarizing copy to creating compelling content, marketing is something I love helping my clients think about. I spent over ten years leading a marketing team in the media industry. Inbound marketing, advertising, and event activation/sponsorships are in my blood. 

One of my clients was struggling to build an annual content calendar and had brainstormed a bunch of ideas she thought were failures. She had been focused on generating one great tagline to describe a year-long program and had what she thought was a list of 10 garbage ideas. I asked her to read them to me. One after another she said the most amazing things that left me wanting to learn more. I didn’t hear a list of slogans or taglines, but a list of succinct, compelling topics. They were all the things she wanted her clients to learn. I told her that she was correct -- she had failed to write a tagline, but she had succeeded in writing 10 of the 12 monthly themes for her content calendar. She only needed two more. Her jaw dropped. “You’re right! These are great! Each one of these could be a monthly theme that includes a live video, a blog post, a newsletter, a guest interview on my podcast, you name it.”

Another client admitted to “getting awkward” during the sales process -- usually right after telling her prospect the cost of her services. “I spend all this time building rapport, and then after I say the dollar amount, I get quiet and business-like and something changes,” she said. “I know they can feel it.”

“Why on earth would you shift your approach halfway through a sales call,” I asked. “Is it because you switched from words to numbers?” 

“No,” she laughed. 

“Is it because you think you’re charging too much?”

“No. In fact, I could probably raise my rates.”

“Then what changed? What’s different at that moment,” I asked.

“I’m scared,” she admitted. “For the first time in the conversation, I’m afraid they’ll say no.”

After that, we found various ways for her to release the pressure and expectations she put on herself going into each sales call as well as to keep her energy consistent when talking about money.

7. GROWTH

Some of my coaching clients have felt like they are “drowning” in the rising waters of change or queasy from the speed at which the business is scaling. Growth is change and change is hard.

There are three types of change -- developmental (when things naturally grow, unfold or evolve), volitional (the boss has updated our sales goal, so we need a new strategy) and circumstantial (we couldn’t have predicted that the volcano would erupt, but it has, so now we run). 

When navigating growth, it’s important for most of my clients to know who or what is causing the change, and whenever possible, have agency or a sense of control over the direction. I’ve heard clients say “I need to reach outside my comfort zone” when skilling-up or moving from competence to excellence. I’ve heard them say, “I need to look outside my bubble” when hiring new team members. I’ve also heard them say, “I know this change is coming. There’s nothing I can do to stop it. And I can handle the growth!”

8. IDENTITY 

Mindset is important for confidence and self-image, but the client must also identify who or what they want to be. If you want to be a rockstar, but don’t see a charismatic leader when you look in the mirror, the audience will know you’re bluffing. They’ll smell it a mile away. If you want to be a successful business owner but think of yourself as someone who “isn’t that good with numbers,” your numbers will reflect it. You don’t have to be Mick Jagger or James Brown to be a successful bandleader and front-person. And you don’t have to be a mathematician to be a business owner. You only have to see yourself as who you imagine yourself becoming.

This is what facilitates change in an individual, when the smoker commits to the vision of themself as someone who doesn’t smoke. This is what facilitates personal and professional development, when the administrative assistant commits to the vision of themself as the VP of Operations. They do the things and make the decisions that person would. They surround themselves with the kind of people that person would hang out with.

This is important when developing vision and purpose in business. Knowing whether you are an accountant or a “fractional CFO to experts in the manufacturing industry” can make all the difference in the way you position yourself, talk about what you do, and connect with prospects.

I’ve heard clients say, “I now know what kind of leader I am and it feels good.”

One of my clients was a former therapist who had transitioned to a group coaching model. She was excited and intimidated by the Wild West of the unregulated coaching industry. She had spent years following guidelines; encouraging her patients to lick their wounds and talk about their worst times; avoiding giving direct advice, not making recommendations about helpful resources, books or podcasts; and not sharing or disclosing her own story. Now, as a coach, she was expected to do the opposite of all those things.

Her inner therapist would raise its fearful voice and tell her it wasn’t right to do those things. It would say she wasn’t qualified and that she might cause harm to someone by giving them the wrong advice or by being too tough on them. She was in a real identity crisis. One day, she had enough. The desire to grow her limitless coaching business far outweighed the desire to battle with insurance companies over copay, and she said, “That’s it! I’ve got to tell my inner therapist to back off when she says I shouldn’t do those things. I’m a coach now.”


If you’re interested in hiring an executive or business coach, sign up for the Amplified Executive Coaching program here. See you on our next call!