As a salesperson early in my career, I recall nights as I attempted to drift off to sleep, thoughts scrambling around in my head about the day. I would toss and turn as I worried about things I had done wrong that day while obsessing about doing the right things after I woke up the next day. Was my customer about to choose my competitor? Where was I missing business? Had I pissed anyone off?

Lord knows, sales people have it rough at times.

So I set out to find out what was on the mind of over a dozen Silicon Valley sales leaders by asking the question, “What are the biggest fears and challenges salespeople face?”

Below are the answers, and as usual I’ve shared my perspective on how you can develop new ways of successfully moving past them.

1. Fear of calling on C-level executives

What do I say when I call him or her? Often the biggest intimidation factor calling on executives is self-confidence, “Am I qualified to speak about their specific needs?” We fear rejection and being shut out for a long time. The more important the situation is, the more we question and doubt. Psychologically, this brings up our fundamental fears around being of value.

Solution: If you say, “Can we meet so I can pick your brain?” You’ll come off as needy. Executives are only human, so start by finding mutual connections or common interests (which you can find via LinkedIn), while being yourself. Next, you MUST take time to thoroughly understand their business as much as possible ahead of time. Research on the internet, get input from manager or director level people in their organization, or ask your own marketing executives for market data.

Finally, continue your pre-call planning to identify the areas where you can bring value – it may be market intelligence, technical expertise, or an introduction to someone who can help them succeed. Repetition is key – the more executives you meet, the more experience you’ll get from successes and failures, and the better equipped you’ll be for future engagements.

2. Fear of losing control of the deal

Many factors involve winning or losing a deal, and only a portion is within our control. Often attempting to control more than we should leads us to overwork, stress and burnout. We talk about time management, but often it’s really about delegating. Relying on other people is challenging – yes, there is joy in winning together and there is power in delegating, but sometimes it is simply easier to do it yourself. Or is it? Sometimes we don’t trust that others will get it done right, that if they make a mistake then we’ll lose credibility as a leader, and with our customers.

Solution: We all have laundry lists of tactical items and it’s easy to lose sight of the big picture. Start by taking a step back and taking on a strategic mindset. Put together a plan for each major customer, answering questions like, “What kind of partnerships and executive alignment do we need?” And “Where do we want to be with the customer a year from now? 5yrs from now?” Next, identify where you are and where to go from there, getting input from your key stakeholders.

Give yourself “strategic breaks” – walk around the building or go for a drive – just get away from your desk so you can stop and evaluate. Next, you can start delegating smaller tasks to your support team. Take time to communicate the desired outcomes to those to whom you are delegating so the goal is clear. Follow up to see how it went and course correct along the way.

3. Fear of unanswered emails

The global economy is 24/7 and the expectations are high. Our customer might be overseas and looking for a response from us the next morning. We try to get home at night and tune out but that can get us into trouble. We fear that if we do not answer emails right away is the customer will move to our competitor. Internal emails from our management plague us on nights and weekends. So we end up doing emails at midnight or laying awake in bed with our Smartphone lighting up next to us.

Solution: While it may be unrealistic to tune out completely, often our fears are irrational. As Mark Twain once said, “I am an old man and have known a great many troubles, but most of them never happened.” If you’re worried that your customer is upset about response time, then ask for feedback regularly. If it never comes up, you are probably being paranoid.

Another strategy for night and weekend email is to scan your email to keep an eye on things, but ONLY reply to things that are urgent. If it is not urgent, do nothing(even if it would take 2 min), otherwise you’re setting a precedent that you’ll be answering all emails. If it’s an email from your boss, shoot them an email back acknowledging you’ve received it but that you’ll address it with them the next day.

4. Fear of cheesy networking events

Most salespeople like to meet people whom they can help and get value in return. Yet we often dread networking events and we often only see “the schmooze factor” where conversations can seem fake and contrived. Often networking is seen as a necessary evil where we think “I just need to get through it.”

Solution: Instead of looking at networking as a superficial card-swapping event, decide to be authentic and curious. Go below the surface by genuinely asking deeper questions about their business, and then find ways you can be of service with what you know. Often we are looking for a way the other person can help US. Flip it around and make it a goal to find a way to help others succeed. Amazing things will happen when you try this.

Ultimately, there are many fears that sales folks go through in a given week, and I hope this has provided some value to you. Please share a comment below on what moved you, or if you have another common fear to add to the list. I hope that we can all help each other move through fear to be the best and most successful we can be.

Author's Bio: 

For over 15 years, Justin McSharry has worked with organizations in a variety of ways to make an impact. He founded EvoLeadership Academy from his passion for facilitating change in individuals and organizations who are ready to make a bigger impact in their business and with their stakeholders. Justin is a lifelong student of human potential and his multi-dimensional corporate background includes engineering, training and sales in the fast-paced and highly competitive Silicon Valley. He’s engineered multi-million dollar technology deals, facilitated and lead training, all while developing his peers through mentoring and coaching.

Justin brings a calming, realistic, and supportive presence to all of his engagements so that clients feel heard and inspired to take their next developmental leap. He’s happily married and enjoys practicing meditation, making music, and traveling.