How can We Encourage Experimentation and Risk Taking Among Our Employees

This is one of those stories that we hope never happened with us.

I was a fresh graduate with no experience and in my first job. I had decent success in my first job and had reached a point where I had built enough trust with my boss that he allowed me to run one of his branch office. As part of the role, I was supposed to handle sales and procurement both. And in my eagerness to do well for my company, I sold a specific product to a customer at a price that was deeply discounted (I quoted the price of a different quality of the same product) and so got the order confirmed. It is only when I informed my boss, that he realised the mistake I had made. What he did then has shaped my entire career.

First, he asked me if the customer has confirmed the order. When I said that I have a confirmed order, he asked me to dispatch the order as per the agreed terms. He asked me to talk to the customer to check if he could make some payment upfront as an advance, if possible. Try to get this done, without any discussion of the price or the mistake that was made. If it works, it works, if not, it is fine as well. As it happens, the customer agreed to pay 30% of the invoice value as advance. We dispatched the material as per the price I had quoted.

When I met my boss the next time (he was in a different city), I profusely apologised for my mistake as the loss on account of the single order was more than 10 times my annual salary. He said, it is ok to make mistakes as long as you learn from the mistake and don’t repeat it. Your making mistakes shows that you are willing to take risks and push boundaries. This is good for both you and the company.

This one conversation helped me realise (now when I look back) the importance of taking smart risks and that it is ok to fail and mess up, as long as you learn from them. This also taught me that as an entrepreneur, it is important to teach and allow our employees to take smart risks and push boundaries.

The question is what can we do to create a culture where not only is this ok, but is encouraged.

Before we go ahead, we need to understand what I mean by smart risks. First step is to redefine the term risk. Instead of calling it taking risks, we are much better off, calling them experiments. So, what kinds of experiments are smart experiments that we want to encourage our employees to take.

S – Simple:

We need to teach our employees what a simple experiment is and what is not. Any action that the employee takes that is self-contained, the risk associated with that is a simple risk and the experiment is a simple experiment. Any action that can have an impact on multiple sides of for business and can’t be self-contained is a complex risk or a complex experiment.

M – Manageable:

Any experiment that if failed, has the potential to threaten the business or a significant part of the business is non-manageable and the employees need to come us as entrepreneurs with such ideas and we should decide if we go ahead or not. Any experiment that is small enough that even if it fails, it doesn’t threaten the business, is a manageable experiment. It is always a good idea that we start encouraging our employees to start with experiments that have minimal downside and then  continue to increase this limit for employees as they become more experienced. We can also start with certain limits within which employees are encouraged to experiment.

A – Astute:

Any experiment is an astute one if it has a potential upside irrespective of what the actual results of the experiment are. This only comes with experience and we need to teach our employees to design experiments which are astute. Once they learn to design such experiments, we can allow them to continue to increase their scope, gradually.   

R – Retractable:

If the experiment is designed in such a way that they are retractable as and when needed, they are retractable experiments. These are by nature simple and contained and can be easily retractable. These kinds of experiments serve as good starting point for employees to build their experimentation muscles.

T – Teaches something (irrespective of failure or success):

The goal of every experiment is for us to learn something valuable – irrespective of the experiment’s results. It is important that these teachings are not contained with the employee who ran the experiment but the learning is shared with all the employees, so they all learn from the experiment.

It is not enough for us as entrepreneurs to define what a SMART experiment looks like and how to design one for our employees to start experimenting. We need to walk the talk.

It is in this context that I would like to share this analogy:

Are you a Lifeguard or a Swimmer?  

Dave Burgess, author of Teach Like a Pirate (2012) asks this great metaphorical question about whether or not you are walking the talk.

He explains: 

“Lifeguards sit above the action and supervise the pool. Although he or she is focused, there is a distinct sense of separateness both physically and mentally. In contrast, a swimmer is out participating and an integral part of the action.” (pp.14-15)

We need to model the behaviour that we expect of our employees and at the same time, recognise and reward the behaviour that we expect from our employees. Without reward and/or recognition, this will just become one of those things that we say and everyone listens with both their ears (in from one and out from the other) and nothing changes.

The reward for having enterprising employees who are willing to design experiments to learn and push the envelope is something that all of us entrepreneurs yearn for as this gives us leverage like no other action can. Suddenly, we can find that employees are engaged, trying new stuff and learning from them.

One key insight here is that while we want to encourage risk taking through experimentation, we don’t want to rock the boat. So, it can also help to identify certain areas of our business that are ripe for experimentation and unleash our employees to design and run experiments in that specific area. This restriction and focus at times brings out the best creativity amongst our employees and has the potential to bring in game-changing results for us. This area can change every quarter or half-year, depending upon where in our business do we need a burst of creativity.

One of the most important thing that we can do to encourage SMART experimentation is to acknowledge every effort and coach the teams at the end of every experiment. The coaching can be very simple things like asking them some very pointed questions like the following: 

Coaching Questions at the end of every experiment

1. Why did you design the experiment the way you designed? What other options did you consider before finalising this design?

2. What was your purpose of running this experiment? Did you achieve what you set out to achieve? How? Why not (if the experiment failed)?

3. Given that you have now finished your experiment, what could you have done differently? Did you think of that while designing the experiment? IF yes, why did you not go with that option? What assumptions did you have that indicated you go with the design you went with?

4. What have you learnt from the experiment, that you did not already know? Why?

5. Based on what you have learnt, what can we do differently going forward?


These questions will help the team reflect on their experiment and internalize their learning. Knowing that they will have to answer these questions at the end of each experiment will also force them to document their thinking while designing the experiments, which when they revisit at the end of the experiment will give them a very good sense of what they were right about and where they were off the mark to start with.

This will also show people that we value both successful and failed experiments equally and thereby will encourage more smart experimentation amongst our employees.

What’s Killing our Creativity?

Scene 1:

I was visiting a hospital today to visit someone who is admitted there to get through a minor surgery. He was supposed to check into the hospital at noon on a given date and check out at about 4:00PM the next day. This means that he had to spend about 28 hours in the hospital. Even for these 28 hours when he was in the hospital, when he was officially on medical leave, he was still working. He was checking his email, responding to his calls and even checking his social media feeds (twitter, Facebook, linked and Instagram).

When probed, he asked me the following question –

“What am I supposed to do if I am not checking my emails or my social media feed? Just sit there and do what?”

At that time, I just let that pass but his question kept coming back to me making me think about what would my behaviour be in such a situation? When I thought about it and if I have to be honest, I would have done a few things differently. Maybe I would have scanned my email once in a while to ensure that there is no fire that needs to be put out. I am fortunate that I don’t necessarily have a lot of fire to put out. So, that would not be an issue with me. I would have picked up a book and read it. Alternately, I would have used the time to catch up on a movie.

What would you do if you were in a such a situation? Are you able to completely disconnect from work or from social media?

If you are like most of us, you would have done something similar.

IF we look at this at a slightly deeper level, we can find that we all want to do something so that we feel busy. We want to feel that we are achieving something.

Scene 2:

Now, lets look at a completely different scene.

We are at work and are in a fix over some issue and need to find a solution to fix it. The issue is not something that has a single right way to solve. And the more creative we are, the better the solution could be. We gather our team around in a room and want to do engage in a brainstorming session. The facilitator sets up the context and wants us to come up with creative ideas that could potentially solve the issue at hand.

We try to come up with some regular ideas, that are neither surprising nor creative. Has this ever happen with you?

I can assure you that most people struggle with coming up with creative ideas. I teach design thinking to experienced executives and as part of the workshop, the participants are required to come up with 25 creative ideas to solve a given challenge. It has never happened in over 100 such cohorts that someone has come up with even 20 ideas (forget creative ideas).

While on the outside, these two scenes may seem to disparate and not connected, research indicates that one is the cause for the other. The fact that we almost always opt to staying busy all the time is probably the cause of the difficulty in coming up with creative ideas. 

Among many qualities that suffer, recent research shows creativity takes a hit when we are constantly busy. The ability to switch between a state of focus and daydreaming is an important skill for being creative. Constant busyness has a significant impact on this ability, thereby making it more difficult to be creative.

Stanford’s Emma Seppälä writes

The idea is to balance linear thinking—which requires intense focus—with creative thinking, which is borne out of idleness. Switching between the two modes seems to be the optimal way to do good, inventive work.

We now consume up to five times as much information as 25 years prior; outside of work we process roughly 100,000 words every day. This saps us of not only willpower (of which we have a limited store) but diminishes our ability to think creatively as well.

Creativity engages the brain’s daydreaming mode directly and stimulates the free flow and association of ideas, forging links between concepts and neural modes that might not otherwise be made. Creativity is all about making non-obvious connection between disparate and disconnected ideas. So, we will struggle to be creative if we are unable to access the daydreaming mode as and when we need. 

This is impossible when every free moment—at work, in line, at a traffic light—we’re reaching for our phone. Our brain becomes habitual to constant stimulation; we grow antsy and irritable when we don’t get that stimulation. At this time we can be sure that we’re addicted to busyness. 

And that’s not so good for us, specially when if we are required to be creative at a moment’s notice. As Seppälä points out many of the world’s greatest minds made important discoveries while not doing much at all. Nikola Tesla had an insight about rotating magnetic fields on a leisurely walk in Budapest; Albert Einstein liked to chill out and listen to Mozart on breaks from intense thinking sessions and even play his violin.

If being creative is important for us, we might have to engineer scarcity in our communications, in our interactions, and in the things we consume so that we have time to allow boredom and allow our minds to wander. Otherwise we run the risk of our lives becoming like a Morse code transmission that’s lacking breaks — a swarm of noise blanketing the valuable data beneath. 

So, the question that we need to ponder is the following:

How to disconnect in a time when connection is demanded by bosses, peers, and friends?

  1. Make time for a long walk without our phones. Incorporate this as a daily routine.
  2. Stop taking our phone out at every opportunity. Start with deciding not to take our phone out when you are waiting for the traffic light to turn from red to green or when we are waiting in a que at a shopping mall to pay for our purchases.
  3. Make more time for fun and games. It is well-known that taking time and having fun by playing games resets the focus and activates the part of brain that is responsible for creativity.
  4. Alternate between doing focused work and activities that are less intellectually demanding. Schedule downtime after every session of focused activity. It could be as simple as taking a 15 minute break before engaging in yet another activity that requires us to focus.

If our work requires us to be creative-on-demand, we need to exercise our creative muscles as well. We would be well off if we make it a part of our daily routine to come up with a set of creative ideas (irrespective of whether we need them or not). This is very similar to digging a well, much before we need water to drink.

If we spend enough time in a state of frenetic shallowness and we run the risk of permanently reducing our capacity to perform creative work.

That’s not a good sign for those who wish to perform creatively, which in reality is all of us and more specifically is a bad news for all of us entrepreneurs.

Research shows that the fear of missing out (FOMO) increases anxiety and takes a toll on your health in the long run.

Of all the things to suffer, ability to think creatively is one of our greatest losses. As entrepreneurs, a flexible mindset, open to new ideas and approaches is invaluable. Losing it just to check on the latest tweet or post an irrelevant selfie is an avoidable but sadly sanctioned tragedy.

Finally a Mixed Reality Tool That Has the Potential to Bring MR in Mainstream Use


Disney Research recently released a white paper on its experiment with Mixed Reality and Augmented Reality. They address the one challenge that was stopping the widespread adoption of Mixed reality in everyday business scenarios – the requirement that the user wear an expensive device on his self and thereby literally get transported to a different world and it was an isolated experience for this user.

They say:

We create a solution for multi-user interactions in AR/MR, where a group can share the same augmented environment with any computer generated (CG) asset and interact in a shared story sequence through a third-person POV. Our approach is to instrument the environment leaving the user unburdened of any equipment, creating a seamless walk-up-and-play experience. We demonstrate this technology in a series of vignettes featuring humanoid animals. Participants can not only see and hear these characters, they can also feel them on the bench through haptic feedback. Many of the characters also interact with users directly, either through speech or touch. In one vignettŠe an elephant hands a participant a glowing orb. ŒThis demonstrates HCI in its simplest form: a person walks up to a computer, and the computer hands the person an object

You can have a look at the video that was accompanied with the white paper here:.

As you can see, the experience with this “magic bench” is not only simple but also has the possibility for multiple people sharing the same experience.

Once the Disney team is able to build this to scale, I can see many applications of this in the real world.

Some of them could be:

  1. Customer Service: Augmented reality customer service engagement at different retail stores. This experience can give the consumers a reason to visit the store rather than buy everything online.
  2. Movie promotions: This will allow Disney and other movie franchisees to allow their customers to have an interaction with their favourite movie characters.
  3. Book Promotions:  Just like there can be an engagement built with the users favourite movie characters, people can also interact with their favorite book characters and maybe the authors themselves.
  4. Mass personalization of Brand advertisements:  Brands can use these benches to hyper-personalise their by immersing their consumers as part of the advertisement itself, there by creating stronger bonding with the brand.
  5. Stories abound: Add to this an AI bot that can engage with the user and have an improvisational dialogue and co-create a story with the user. This would just be amazing to see. We could have a “Whose Line is it anyway” with a virtual character in play (played by an AI bot).

These are just a very few ideas that I can think of.  I am sure you can think up a lot more uses for these magic benches.

I see enormous potential for this technology if this is developed and opened up to entrepreneurs to play with.

The question is will Disney make it available for developers and entrepreneurs learn and play with their creation?

Does Your Business React, Respond or Create?

Bernadette Jiwa wrote a short but insightful post about the difference between responding and reacting to situations.

She writes:

It was impossible to walk down any high street in June without running into a notice informing you fidget spinners were BACK IN STOCK. The fidget spinner was clearly ‘thething’ of the moment. A month later we’re already beginning to witness its decline. Another fad bites the dust.

A fad by definition is transient. It’s success hinges on what people are talking about today and is not backed by a genuine need that will require to be fulfilled tomorrow. It takes effort and courage to respond to everyday needs instead of following the crowd that’s reacting to what’s top of mind. It’s impossible to do both—which is why a good business strategy is always intentional.

This is so typical of her to raise such important issues in such a short and poignant manner.

I would just add one more dimension to this question

Is your business reacting, responding or creating?

Generally speaking, we see three types of businesses in the market-place.

Self-obsessed businesses:

These are businesses that are obsessed with themselves and what they want to do. These are typically businesses that are founder driven and the founders have a strong vision of what they want to do with their business, whom do they want to serve, how they want to serve and go about running their business accordingly.

Competitor obsessed businesses

These are businesses that are obsessed with their competitors. They use their competitors and their position as the driving energy to do what they do. They want to be better than their competitors. They go after the same customers as their competitors and they want to win the market and surpass their competitors. These lead to markets where there is intense rivalry between the players.

Customer obsessed businesses

Then there are businesses that are customer-focused. They identify a customer segment that they want to serve and then go about solving all their needs. They dont define themselves as they are in a specific kind of business or a specific industry. They want to know their customers really well and want to continue to grow by solving different problems for the same customers.

We can all think of businesses that could fall in either category and are immensely successful in their own rights. So, none of these are necessarily good or bad way to run a business. What is important is that we as entrepreneurs know and are deliberate about what kind of business we are building.

Irrespective of which kind of business we build, we still need to answer the question:

Are we reacting, responding or creating (to/for our customers, competitors or our own aspirations) ?


Reacting gives the power to the other. We are dependent on the customer/competitor or flashes of insights and aspirations to do something new.

Stimuli  —-> Reaction


Responding gives the power to us, in terms of how we respond. We can be deliberate the right action, but still needs a stimuli.

Stimuli —— (Deliberation and choice) —> Response


Creating rests the power completely with us. We dance to our own music and rhythms. We are setting the pace and owning the outcome. There is no need for an external stimuli which needs a reaction or a response. This is the reason, I believe that as entrepreneurs, we need to be operating in this realm more often than not.

This can only happen if we are deliberate and intentional about how we run our businesses.

So, are you reacting, responding or creating?

What to Do When You are Having a rough day?


Being an entrepreneur is not for the faint hearted. As entrepreneurs, we are constantly trying to juggle things, fighting fires, digging wells, selling ideas and influencing people. IN the midst of doing all of these, there are days when nothing seems to move in the direction that we want them to move in. Worse still, things move in the opposite direction. Every meeting, every phone call, every email leads to a response that is exactly opposite to what we were hoping for. We miss an important deadline and in the midst of all of this, our spouse or the significant other or an employee calls up and we end up taking out our frustrations and anger on that person. This is so uncool.

We all have these days. So, the question is what can we do about these days? How can we deal with the anxiety and the frustrations that these days bring to us?

These are a few things that we can do:


The first thing that is critical is that we acknowledge that we are having a rough day. Then tell ourselves that this too shall pass. We need to practice empathy towards ourselves as much as we need to practice it with others. Once we acknowledge this feeling of frustration and anger, we can start work towards managing this stress levels.  One thing that has worked for me in the past and is recommended by Benjamin Zanders in his book “The Art of Possibility” is to practice telling ourselves – “How fascinating” and then go on to see what is so fascinating in the scenario. It can help even better if we see the entire thing with a third person view (view as if this is happening to someone else and not us).

Slow down:

Once we have realised and acknowledged that we are having one of those days, we need to stop working, slow down and start breathing. One of the physical aspects of being stressed is that our body starts reacting to the stress physiologically by releasing certain specific harmones. The way we deal with these harmones is to slow down the release of these stress harmones and then release the harmones which will help us in dealing with stress.

We can do that by slowing down and breathing. I dont know if you have noticed this but everytime I am stressed, I start pacing around, the speed at which I talk increases, everything about me seems to be faster. This includes the speed at which I can think of everything else that could go wrong as well.

So, it would be a good idea to find a place where we could sit down comfortably and sit down. Then practice deliberate, slow and deep breathing. We all know that the body and mind are interconnected. The body follows the mind and the mind follows the body. So, the moment, we slow down physically, our mind starts to slow down as well. This by itself is a great step and will work even if you dont do anything else.

Or Speed Up:

Some of my friends find it extremely difficult to slow down in such moments. So, the alternative if we can’t slow down and practice deep breathing, we should find a way to speed up. We could go for a run, hit the gym or go for a session of swimming. The idea here is to get the physical body & the mind to start focusing on something else.  This activity also ensures that our body gets a lot of oxygen and has a similar effect on the physiology of our body.

Make a phone call:

One of the next thing you could do is to call someone. Ideally, this is someone whom you have already identified as the person whom you will call in moments such as this. This could be a friend, a partner, your spouce, a therapist or your mentor or a coach. The idea here is to not continue to dwell on the day and take perspective. This is where being part of a mastermind group or a coach can be a big help. You could share your frustration with them and they can at best give you a different perspective and at worst listen to you and tell you that everything is going to be all-right.

The closer we are to a problem the more unlikely we are to solve it. Stepping back gives a better perspective. Taking the mind off the situation helps in coming back to the problem with a more refreshed and active mind. The trick here is to call the right person – it is best if we already have a set of 3 or 4 people identified for such situations ahead of time. It works even better is you have already shared with those people that you will call them in situations like this and if it is ok for them to just give you the 10 – 15 mins of their undivided attention at that time and help gain perspective if possible.

Trigger a habit:

We are all creatures of habit. There are certain habits that can trigger certain thought patterns or a series of actions and behaviours. For example, if I start listening to a specific track of music, it automatically puts me in a mental frame and I relax. I also like to walk to my cafetaria and engage in the process of making tea for myself. That by default slows me down, puts me in a very contemplative mode and takes me to a very different place. Doodling does this to a lot of people. Watching news does something similar to people. Watching a scene of a favorite movie has a similar effect for some. This is also the reason why most people go out for a smoke when stressed. That is not the habit that i would want any of us to invoke.

IF we don’t have one such routines, maybe it is time for each one of us to be intentional about creating some such routines or habits that can help us in managing these situations.

Find Small Wins: 

Everything that we have discussed so far is about stopping ourselves getting stressed. That is never enough. If we dont create something that can take its place, it will return the moment we are done with all the above steps. So, it is important for us to find a way to reverse the stressors. This can be done by two ways. The first is for us to find some small wins and celebrate them.

It could be clearing out our inbox or sending a hand-written thank you note to one of our important customers.

It could be crossing something from our task list.

It could be as mundane as taking care of some of our chores that we have been procrastinating about.

The trick here is for us to find some small win that we can celebrate. This celebration is what has the potential to stop the stressors and put us in a positive frame of mind, which can then trigger other smaller wins and so and so forth.

Practice Gratitude:

The other way to reverse the stressors is to find things that we are grateful for. At times, this seems so difficult to do. Having a gratitude journal is something a lot of us find difficult to maintain. However, I have found that developing this habit of writing a gratitude journal can have significant benefits. Every time, we are in a situation where nothing is going right, reading this journal immediately puts things in perspectives. It tells us that there is a lot that is going our way than stuff that is not going our way. Just this realisation that there is a lot for which we are grateful for has the effect of reversing the stressors.

The key here is that we need to cultivate the habit of gratitude journals before we end up in a situation like this. Though, thinking about what we are grateful for, in such situation also has benefits, the real and lasting benefits come from having this practice already in place and doing this with full sincerity. We can fool everyone in the world but ourselves. So, if we are not truthfully grateful for things that we write in our journal, the entire process is counter-productive and will cause more harm than good.

Be a Philosopher Entrepreneur: 

The most difficult but the most effective way to handle days like these are by being a philosopher. In Indian mythology, we have a consistent theme, where we are asked to do our work and not expect anything else in return. The implicit and sometime explicit meaning is that what we do is in our control and we do that. What comes out of that action (every action has a reaction) is not in our hands. We just need to accept whatever comes back as is, without judging if it is good for us or not, if it was fair or not. The moment we are able to suspend judgement if the reaction for our action was favourable or unfavourable and always take it as the best that could have happened, we are not allowing ourselves to get stressed at all.

This is somewhat similar to ourselves being in a permanent beta. We evolve with every iteration (everyday) of living our lives. We get better with every iteration (everyday) as long as we learn from the feedback that we got the previous day.

In Conclusion:

As entrepreneurs, we will have always have things that will not go as we want them to. Some days, this will be much more prominent and happen multiple times. Staying relaxed and calm during this time is the key to not doing anything stupid. A calm and composed demeanour will take us in the right direction.

What we need to do is to know that this will happen sooner than later. So, it is better for us to be prepared with a specific routine that we will engage in, when we enter such a situation, This will help us deal with such situations much better and we feel more relaxed knowing that we have a routine for the bad (so called)  days already built-in.