Conquering the three big fears in enterprise sales


I can’t believe that 2018 is nearly over ! I have been checking in one folks that I mentor for the last couple of weeks to see how well everyone is doing before we all head for vacation time. Those with a sales quota that hasn’t been retired generally are on an overdrive of emotions in December – positive or negative.

Even for experienced sellers – occasionally, fear of not retiring their quota becomes a paralyzing issue . For inexperienced ones – I have noticed it to be fairly routine. I thought I will share my thoughts on this topic here

There are three big fears to overcome in enterpise sales

1. Fear of inertia

This has two flavors to this – external and internal .

Most customers hate change unless they are sitting on a burning platform. It’s not enough that you think there is value in what you are selling – you need to validate (and sometimes repeatedly) with the customer first hand that they see the value in moving to your solution.

The internal flavor can cause just as much anxiety – especially in larger companies with complex and rigid approval workflows . I have fallen victim to this when I started out – I was more afraid of our internal finance and ops reviews than about negotiating with actual client. That fear went away thanks to a mentor showing me that no reviewer knows my deal as well as I do and that if I can confidently explain it , the inspection session can be turned into a coaching session . As I gained experience – it also helped me challenge some processes and get them changed

2. Fear of competition

From my own experience as a young seller many years ago, and then later as a leader of sellers – I have data to prove that the biggest threat to your proposal not getting ink on paper is customer inaction, and not competition . Ergo – the lack of thoughtfulness in crafting your value prop , and lack of customer relationship are way more serious threats to your success than your competition . Those are both within your control to get better at !

There is one thing I insist with my team all the time – ALWAYS respect your competition , but NEVER fear them . If you don’t respect them – you just are increasing your blind spots and you won’t know what hit you. If you fear them – you will focus more on their strengths and weaknesses and not yours .

Price is a big reason why people worry about competition. A larger competitor might be able to offer a lower price than you could . Even the client might tell you that they are just looking for the lowest price . However – that doesn’t mean you will win if you have the lowest price ! There are always more parameters to differentiate and it’s your loss if you become one dimensional and fight the price war and race to the bottom. The one who wins is the one who understands the customer the most , not the one who understands competition the most !

3. Fear of the clock

Especially in December – this is the primary fear for most sellers . Will I be able to close this deal before end of the year ? Even if customer sees value and has recognized that you have a better proposal than others – they still may not choose to buy immediately.

This happens commonly when your value prop doesn’t account for the time dimension at all. If you only realize this late – you can still get a deal done by creating incentives like discounts , or asking for a favor with the relationships you have hopefully built . But those are all suboptimal in general for you and the customer . The better way to do it is to understand what is the most logical time for the customer to do the deal and then consciously (without time pressure) determine a good way to accelerate the deal closure .

Conquering the three fears

It’s absolutely possible to overcome these fears . I suggest the following as a starting point

1. Spend your energy qualifying your deals every step of the way from the moment you identify them .

2. Invest in understanding your client, your competition and your internal organization – in that order

3. Remember it’s a team sport ! Your manager and a lot of other people have a vested interest in your success – the sooner you make use of help available, the better your odds of success . Heroics should be a last resort , not your leading card

4. Never lose perspective of business cycles and luck . If 80% of deals work as planned – you should be happy

5. Never burn bridges – enterprise is a small market and you will see the same people again . The most difficult CXO I ever sold to bought from me at three different companies – and I was within an inch of yelling at him for what he did the first time I met him 🙂

6. Never lose your moral compass. There is more to life than any one deal !

For the love of dogs…and dog shows


I have loved dogs all my life. When I was born – there was a big German Shepherd in the family who was gifted to my dad by his aunt. He passed away when I was three or four. My own first puppy was “Toffee” – a Spitz – whose breeder was a student of my Grandfather, and had heard me asking my grandfather repeatedly for a puppy. I must have been seven or so at the time. Someone stole Toffee from our house – and this disaster repeated one more time a few years later with Timmy (also a spitz). The way I dealt with the trauma was by rationalizing that I will never keep a small dog ever – and thus eliminate the chance of my furry friends ever getting stolen. That strategy worked out so far – keeping fingers crossed.

Thus entered Betsy into my life, the sweetest and also perhaps the most disobedient dog that ever lived in India 🙂 . She was a yellow Labrador that my dad bought for me ( as a result of significant drama I created at home) from Bangalore. She also was my first show dog – and her very first show she won Best of Breed and CC, and placed in the BIS lineup. I was hooked to dog shows. I bred her only once (I was a mature tenth grader) – and she had one champion from that litter – a black male. Unfortunately the best puppy in that litter died at 4 months . Raising that one litter proved to me beyond any doubt that breeding is way more trouble than I can handle.

Showing in the breed ring seemed way too much fun – and I had several friends who were shy to get into the ring themselves and were happy to let me do the honors. So my handling skills improved rapidly and I won my fair share – including winning BOB at the Nationals and so on. Some of my best friends in India are folks I met in the sport – some my age, but many decades older than me. Some were real princes, senior politicians and bureaucrats, some ran some of the biggest businesses in India at the time. They all treated me like a son – and not only did I learn a lot from them about dogs, I also gained tremendous confidence in dealing with senior people at a very young age – which helped me a lot as I started my career.

I also owe sincere thanks to uncle Radhakrishnan, who is an eminent dog show Judge in India, for talking me out of dropping out of school to be with dogs full time. He was the one who told me “Go finish college and get a job – you can have any dog you want”. Just for reinforcement – he added “And if you do drop out now – I will make sure no judge in India will let you win in the ring” . He denies he ever said the second part 🙂

While breed shows were fun – my heart was always in the obedience ring. My lab was a great teacher . She was the reason I quickly figured everything about how not to train a dog 🙂 . As luck would have it – right when Besty had a litter, I got myself a male German Shepherd puppy. I called him Hitler ( Not in honor of the bad guy – but in honor of the best obedience dog in the country at that time, a male yellow lab who was a working police dog in Railway Protection Force ). We had a grand time – training every day even when I was sick. One of the smartest decisions I made was to teach him commands in Hindi – when every other dog we competed against used English commands. He had laser focus – and we beat every team in India at the time we competed against.

My proudest moment was when Abdul Khadar (the guy who trained the yellow lab Hitler after whom my kiddo was named) watched us in the ring – and told me with tears in his eye that my dog did even better than his dog (who had passed away by then). More than our wins in the obedience ring – he was my heart dog. He was also quite a star in the community . The local newspaper even came out with a Sunday supplement in his honor.

The one skill I acquired training him was that you can solve any problem by breaking it into very small problems that can be easily solved and then put it all together for a grand solution. Best example was that I trained him to pick up a grocery bag and run to the corner store and buy a packet of milk in the morning. It took several months to get there – but he was foolproof once he learned it. That is a principle that has helped me throughout my life – and not just in training dogs. Hitler was almost 10 years old by the time I moved to the US. One of my biggest regrets was that I could not find a way to get him here with me. He passed away a couple of years later – and I will never forgive myself for not being with him when he left this world.

With the first salary I got in US – I bought a German shepherd in Germany . Inka stayed with my buddy Dr. Satish in Bangalore and was his best buddy till she died. Unfortunately we could not get a puppy from her. Since then I have owned or co-owned a lot of dogs across the world. Some in India were even in the name of my little sister Lekshmi – without her knowledge 🙂 . When we got married, my wife was afraid of dogs. But the day we got a puppy in 2005 – she magically transformed to a big dog lover. And then she was instrumental in getting the next two fur kids 🙂

One thing eventually became abundantly clear to me – I could not honestly say any more whether I loved my dogs more than I enjoyed the game of dog shows. I came to the conclusion that its a lot more fulfilling to prioritize my dogs over the game. I still buy purebred pups with show potential. I give them every chance to do well in the show ring. But unlike in the past – I care nothing at all if they win or lose. They all retire from the ring early and enjoy being pampered full time. I still enjoy shows – even if I don’t show myself. I just go hangout with my friends and watch from ringside. Side benefit – I am not affected by dog show politics either 🙂 .

Now life has come full circle again. My youngest dog Ollie is not obedience trained at all – which is not good for any family dog. He is our full time hugs-and-cuddles-machine 🙂 . And I have only myself to blame for that. My 10 year old black lab Hobo could have perhaps been an obedience champion but I completely lost interest in shows and just did not move forward with him.  I recently revived connections with my old friends in the German shepherd world. I am itching to get a puppy and start IPO (working dog) training . If only I could make up my mind……and convince my family 🙂

Getting the most out of review meetings


Yesterday night, I helped a couple of colleagues prepare for reviewing their deals with their line management. And today morning I spent some time reviewing a couple of deals with my team. Perhaps the largest category of meetings in the corporate world is “reviews” – be it deals, career, special assignments or whatever. Having been a reviewee and a reviewer several times, and having been in both good and terrible reviews, I thought I should jot down a few thoughts on this topic.

group of people in a meeting
Photo by rawpixel.com on Pexels.com

For the reviewee

  • Have no fear : This is absolutely the key to having a good review. Bad reviews are most often a result of fear. Reviewers often (not always) know way less about the topic at hand than you do – which is why they asked you to work on it in the first place. If they sense you have some fear, they often think that is because you have not done a good job thinking through the problem. So someone will start poking at your POV and then the herd mentality will kick in and soon they are all jumping on your throat. Don’t let that happen – walk in prepared. And call out risks and open questions explicitly. Ask for additional help as needed. Tell them what you have already done before asking for help. Do whatever you need to do up front to prepare – except pls don’t EVER resort to lies – and it will pay off in spades. Also, if you develop a reputation for coming to reviews well prepared, you will have their confidence and reviews will start getting more pleasant for you.
  • Know what a good outcome is before you walk in :  

    “Would you tell me, please, which way I ought to go from here?”
    “That depends a good deal on where you want to get to.”
    “I don’t much care where –”
    “Then it doesn’t matter which way you go.”― Lewis Carroll, Alice in Wonderland 

    The success of a good meeting is in knowing what a good outcome looks like. It could range from you living to fight another day all the way to getting funding approved for a key project. If you don’t know what you want from the meeting and leave it to just play out – the odds are that you will end up with a result you won’t like, or at a minimum asked to come for another review . When I prepare for a review, I work backwards from what I want out of it to prepare my narrative. When you walk in prepared and without fear – you often pick up things to learn from what the reviewers tell you. That is the highest value of reviews – the learning and tweaking of what you already knew!

  • Always have options : People are unpredictable in generally, and especially so under stress. So all that prep you did might not come in handy when there is someone in the review team who is having a bad day and is hell bent on taking it out on you. In less drastic situations – they still might want to “add value” and you need to leave some room in your solution to incorporate their input. One way to solve this is to pre-determine a couple of areas where you could use some coaching, and explicitly state it in the review. Also – figure out your strategy in case the review goes south. Do you want to ask for another meeting ? Should you enlist the support of a few reviewers before the formal review?
  • Know what is important for the reviewer for the short term : The needs of reviewers change from time to time. You may be reviewing your deal which has great revenue but not the best profit. If your boss needs more profit and not revenue – you probably are not going to score an approval. It helps to know upfront what is important for the reviewers before you craft your narrative. This obviously needs work in terms of networking and homework. But it is time and energy well spent ! One of my worst reviews came in a meeting that I prepared very well for. I was the lead developer and I got ripped a new one for telling them what I did on performance optimization, when the big objective from the CIO was to have more robust testing accomplished in that quarter (which made sense, but I had no idea it suddenly trumped performance problems we were working on) !

For the reviewer

  • Do you actually need to review ? : Life in the corporate world will be infinitely better if reviewers were honest about their answers. Vast majority of such meetings are low calorie or just gamed for optics. Why bother having such meetings? This is especially true the higher you are in the pecking order. Every review you ask for has several people below the hierarchy spending time on intermediate reviews. Can some of it be automated fully or partially ? Is there a standard checklist that can be used to manage by exceptions ? Can the team be better trained and managed to minimize the times you need to review yourself? The idea is to minimize low calorie reviews – and conserve time and energy for where it is needed the most
  • Does the reviewee know what you are expecting ? :  That is not the same as the meeting having an agenda and the presentation following a published template.  It is easy to ask “gotcha” questions. It is usually low value to do so though. When you give someone a problem to solve – tell them what you expect them to come back with ? Are you just looking for information ? Do you want them to make a decision and solve it – or should they bring back options and you will pick one ? Do you want to know if this is the right problem to solve ? Are there any direct consequences to the not solving the problem that you can tell the reviewee about ? How often should they keep you posted on their progress? The more clarity you can provide and the more consistent you are – the more useful these reviews will be for you.
  • Feedback comes in many forms : Not all reviews are about giving an explicit approval to some proposal. One of the most useful things you can do as a reviewer is to also explain how you viewed the review process itself. Could the reviewee improve on something ? Will you change something about the process because you learned something new from the reviewee? Do you engage in an intellectual debate with the reviewee or do you just check boxes ? . Do you follow up on the commitments you both made during the reviews? Do you use reviews as teaching moments? If you want the next review to be great – you need to make the reviewee feel that it was a good use of their time, and not just an administrative activity.