FAQ’s

 Is a coaching relationship right for me?

The first test is how motivated you are to make a change in how you approach your business. Are you:

  • Willing to challenge yourself?
  • Open to asking uncomfortable questions?
  • Willing to change the way you do things?

The second test is whether you can devote the time required to honor the coaching relationship. Will you commit to and protect your weekly, bi-weekly, or monthly one-on-one coaching appointments? Will you commit to knocking out the action items that may come out of the sessions? We will try to restrict the amount of energy to 2-3 hours a week of active effort working on the business.

Is Highland Ross right for me?

Only you can determine this, but it should “just feel right”. You have obviously taken some time to poke around this website, and you have most likely met Bob in person somewhere in the community, so hopefully you have a good feel for Bob’s communication style and personality. Because business coaching is so hard to describe in words, we recommend spending a couple of hours or so with Bob to explore some of your opportunities and pain points. By the end of the session, combined with all your other data gathering and sensory input, you will know if there’s a connection.

Wow, so many touchy-feely words from a guy with an MBA in finance, huh? Seriously, it (Highland Ross and the coaching relationship with Highland Ross / Bob) has to feel right. If we don’t connect quickly, chances are that we will be just talking past each other, we won’t ever go deep, and you won’t buy into any actions or recommendations that come out of our time together. If we do “click”, amazing things can come out of the relationship for your business, your team, and everybody else in your circle of influence.

What makes you think you can help me; I’ve seen your bio and you don’t have any experience in MY field?

True enough, BUT, while every business and every industry is different, every business is also pretty much the same – they all need to attract prospects, convert them to customers, service them so they come back again and again, hire teams to help run the business and administer and finance it all. Does your business do all those things? I’ve had some amazing experiences throughout my career. Wonderful managers and leaders and terrible ones; great organizations and toxic ones. I have:

  • Worked in the ivory tower of Fortune 500 companies, as well as on the shop floor.
  • Owned a print shop and can relate to business ownership, running to Wal-Mart for T-P in the middle of the night, etc.
  • Earned a PhD from Hard Knock U, and an MBA from Vandy.

All of this is meaningless, though, if you aren’t feeling the empathy and the understanding. Reach out to Highland Ross by phone or the contact box to find out for yourself.

What service is right for me?

Life is a series of trade-offs, and so Highland Ross strives to provide viable services. The trade-off between one-on-one coaching and group workshop-based programs is investment vs level of customization. One-on-one coaching is completely in the moment, unscripted, and free-flowing. The focus is 100% on you, your business, and your opportunities and struggles. Group workshops are more scripted, less in-the-moment, but also require a lower investment. Other benefits to a group workshop program include the inherent “master-mind” conversations that spontaneously happen with your peers who have face similar challenges, as well as the networking component itself.

Whether you opt for one-on-one coaching or a workshop series also depends on how quickly you want results! It also depends upon your availability to invest time and effort into getting results.

For one-on-one coaching, however, we recommend jump-starting the relationships with weekly meetings. We will naturally get to a place where we both know that weekly meetings are overkill and mutually agree to dial things back to bi-weekly or monthly. And, then a new opportunity or brush fire will pop up and we may jointly choose to go back to weekly meetings for a while.

Enrolling in a coaching program is a commitment, and you know nothing great ever comes easily. Regardless of which program you choose, you must be fully committed to taking the actions that move your business forward each week. In return, Highland Ross will commit to providing you outstanding support.

Can I try it out before I make a decision?

Yes! Call today or fill out the contact box to schedule a free, initial two-hour session. During the two hours, you’ll experience the process! By the end of this session, you’ll have specific action steps to begin your journey to “mission accomplishment.” You’ll also know first-hand whether this is the kind of relationship you’ll benefit from without having to guess or take a leap of faith! If after our no obligation, free, initial two-hour session, you decide that it’s not for you; no hard feelings! I’ll wish you the best and we’ll part friends. If, on the other hand, you decide this is a great investment in you and your company, then we’ll finalize the details and get started!

Are there guarantees?

If after your first 30 days of coaching, you regret your decision, you can cancel immediately and get all your money back! Coaching is incredibly powerful, but it does require a commitment on your part. If you “bit off more than you could chew,” it does neither of us any good to continue.

Furthermore, if you don’t believe you were provided value, I don’t want your money! I have limited time for a limited number of clients. For the virtuous cycle of providing value and earning client referrals to continue, Highland Ross needs every single client to be successful! It has to work for both of us.

Where do we meet?

That’s your call. Most people prefer to meet off-site to prevent interruptions and distractions and to ensure maximum privacy. But if you prefer to meet in your office or another place, that’s fine, too. Just make sure you can “be present” and ask your team to respect your time while we are together.

How is business coaching different from business consulting?

Consulting engagements tend to be very transactional and very defined. “Do this”, “fix that”, or “make me a recommendation on the other”. Coaching relationships, as the term implies, are more “relational” and exploratory. Through a coaching relationship, you will gain clarity on your biggest thing and how to attack it. A consulting engagement might naturally follow if you lack the expertise or bench strength to attack “the biggest thing” …but, more likely, you will feel that, now that the big thing has been brought out into the open, defined, and named, you do indeed have the wherewithal to attack the thing internally.

The ongoing nature of the coaching relationship allows Highland Ross to help you build and strengthen the skills and experiences necessary to allow you to handle the most pressing challenges and greatest opportunities in your business.

How should I think about business coaching?

It may sound trite and self-serving, but everybody needs one or more mentors or coaches in their lives. Athletes know this; in team sports, it’s obvious, but look at any of the world-class athletes in “individual” sports like swimming, running, cycling, tennis, or golf. They ALL have coaches who challenge them, show them new ways of doing things, and keep on track and accountable in their training. Coaches provide nurturing and guidance during the slumps and are the first to celebrate the successes.

Business coaching will focus you on the most important business and personal goals and allow you to clearly identify the most powerful actions that you can take to consistently move your business on the right trajectory. Highland Ross will support you in identifying priorities and opportunities and ensure that you remain focused on the most important actions. Highland Ross will tell you what you need to hear, not necessarily what you want to hear. If you know Bob at all, you will know that he is incapable of blowing smoke.

How does the coach-client relationship work?

We build a strong relationship based upon mutual respect and trust. We communicate with candor and without judgement. Take a look at our About Us page and our Core Values  page to get a better feel for who Highland Ross is. The focus of our relationship is identifying actions that will improve the performance and value of the business through greater effectiveness. “The Relationship”, the coaching relationship is THE most important thing either of us has going, and is THE source of value. We must both be committed to and honor “The Relationship”. If this sounds too amorphous, too touchy-feely, too squishy, there might be other business coaches out there who may be a better fit for you.

How long does the typical coaching program last?

We recognize that great coaching involves lasting change, and lasting change takes a bit of time. We encourage clients to make a commitment to a one-year coaching program, but frankly, most find the program so valuable that they continue beyond that original commitment. Our coaching relationship will naturally ebb and flow, but “the Good Lord willin’ and the creek don’t rise”, Highland Ross will be around as your coach and sounding board for as long as you like.

Will my workload increase due to “assignments” given by Highland Ross?

At first, yes, unequivocally yes. But, you will be spending your time working on the highest priorities identified in the discussions with your coach. Bob keeps the assignments manageable and achievable so that you gain momentum and confidence. Very early on, we will prioritize those things which will give you the most amount of breathing room. Gradually, your workload will be decreased to levels before we met. Then, balancing your time between your personal life and work will be up to you. We will go as fast or slow as you like.

Will you provide coaching for clients outside of the Winston-Salem / Greensboro / High Point area?

As much as we want to say yes, it is situational. Long-distance relationships are hard, even with Zoom. There are so many important non-verbal cues that we must both be tuned to, so many nuances.  I used to be skeptical that video conferencing can do justice to such cues, but a year into the pandemic, I am a believer.  My default position, however, remains to meet in person.

How is Group Coaching different from One-on-One Coaching?

Group coaching is designed to be more cost-effective and offers clients another option to gain the benefit of coaching while also gaining the benefit of becoming part of a Mastermind/peer networking group. We have monthly meetings where we learn about and discuss a relevant business topic together and brainstorm and learn from the entire group. In addition, each member of the group has a one on one coaching session with Highland Ross each month, where we talk about YOUR business challenges and opportunities. This program is very valuable and sometimes clients who have been in a one-on-one program join a group coaching program as well for the value of a “network of like minds” that lasts for years. Frequently, the clients in the Group program become friends and customers of one another for many years to come….

How much does Highland Ross cost?

In most cases, the growth in revenue and profits realized from the coaching relationship more than pays for, (by triple or quadruple) the cost of the coaching program. In fact, the results you receive last for years after the coaching relationship has ended. It’s one of the greatest investments you will ever make! It would cost you more to hire a receptionist to answer your phones for a year, than it will cost you to hire a coach for weekly coaching sessions. Think about that for a moment…

Please call or fill out the contact box to schedule that initial, no-obligation session. At the end of our session, if it feels right to you, we will certainly discuss our pricing in detail.