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.

Declaration of Independence – Here is to the Crazy One’s


One of my favourite ads of all time is the Apple ad – “Here’s to the crazy one’s“. This advertisement is a call to action to all of us who have a creative spark, an idea, the yearning to do something good, the frustration that we are wasting our lives the way we are living them. A lot of us are making a living not living the life that we truly want to live.

I am not calling all of us to leave our jobs or to start a company or to disrupt everything. No. That is not the idea. And yes, if that is what we want to do, by all means we should be free to do so.

The idea is that we should not restrict ourselves and our creativity but embrace and celebrate our creativity and be comfortable with our weirdness or our onlyness. As James Victore says – “What made you weird as a kid is what makes you great now”

The idea is not to conform to a specific stereotype, just because it is the safe thing to do.

The idea is to bring our full selves to whatever we are trying to do and allow or inspire others to do so as well.

The idea is that we allow our ideas to come to life in whatever shape, form or factor that they want to come out.

The idea is about bringing a lot of energy and having fun in whatever we are doing for the majority of our lives (work).

Declaration of Independence:

So, here is the Declaration of Independence for the crazy one’s:

  1. We believe that it is our fundamental right to have fun, be creative and be happy at work.
  2. We believe that it is our right to bring our ideas to table irrespective of our race, colour, sex, designation, experience or sexual orientation and get a fair hearing.
  3. We believe that it is our right to do work that is meaningful to us (as part of our regular jobs or outside of the jobs).
  4. We believe that it is our right to be treated based on the merits of our ideas and actions and not based on any other criteria.
  5. We believe that it is our right to question the status quo.
  6. We believe that it is our right to attempt to change the world – one person, one idea and one day at a time.
  7. We believe that it is our right to question & stand up against things that we believe are not right.
  8. We believe that it is our responsibility to create this culture ourselves and stand up for other creatives and crazy ones.
  9. We believe that it is our responsibility to promote other crazy one’s in their journey.
  10. We believe that it is our responsibility to spread the word and help every crazy one sign-up to unleash their creativity and craziness on this world.

This declaration of independence is as much important for each one of us, the crazy one’s, but also to every one of our family members,  friends, colleagues and the managers. If you know someone who wants to unleash themselves and their creativity in the world, allow them the freedom to do so. Instead of convincing them to take the safe and secure way and to conform to a sterotype, encourage them take their own path to their own future.

Lets go change things!

Lets go change the world for the better!

Most importantly, Lets start doing and being !!

Avoiding Overwhelm – Managing the Workload of Being a Leader

One of the challenges that all entrepreneurs face is managing the workload. Being an entrepreneur is not easy. It takes a lot of time, energy, effort and attention.
In this short video, Amy Jen Su, shares her perspective of how can we manage our workload and still have peace of mind and not get overwhelmed.
She shares the 4P’s that we need to work on individually in order to achieve the 5th P (Peace of Mind):

Personal Operating system:

What she means is how we do operate as an individual.
  • Do we have a single place where we capture everything that comes our way (Landing Pad or Operating System)
  • Do we have a way to sort through this and identify what needs to be done today and now?
  • Do we know what time in the day are we most effective? Can we use this time to tackle the most important and the highest value adding items on our list? Do you manage your calendar in such a way so as to maximizing this energy rhythms?
  • Have we built-in habits and rituals to deal with the highs and lows of our physical energy through the day?


In this part of our professional lives, she talks about the importance of having boundaries.
  • Have we set up your personal boundaries (times when we are available, times when we are not available, when can people expect a response from us, etc. Do you have an emergency protocol (what needs to be done in case of an emergency?)
  • Have we helped the people who work for you set up their own boundaries?
  • Are we comfortable with these boundaries?
  • Does our team have a go-to person for a lot of things? How over-worked are they? Are they becoming bottle-necks for our team and our own productivity?
  • How can we help our people to improve their productivity so we can have more leverage and thereby become more productive?


In this part, she explains the importance of having clearly defined priorities in our lives. She also uses a 2×2 (Passion * Contribution or value) matrix to talk about different tasks and shares a recommendation for each one of the tasks based on which quadrant they fall in.
One could use this matrix or the one that Stephen Covey made famous or any other matrix. I believe the core purpose of each one of these matrices is to force us to look at each of the task that we do and think about it critically and make a choice:
  • Try to eliminate what can be eliminated
  • Try to Automate what can’t be eliminated
  • Try to delegate what can’t be automated and what is not your area of contribution
  • Train to become more efficient at doing tasks where we have the potential for high levels of contribution
  • Enjoy tasks that we are good at, love doing and those that add a lot of value.


In this part, she talks about one of the things that most of us struggle with. This is about being present in the moment,  giving someone or something our total attention and focus.
  • How long is our attention span? Can we increase this using meditation or training?
  • Do we have any “visible or invisible tells” that can inform us about our attention waning? Can we identify this and learn to bring our focus back.


Amy shares that once we take care of all of these 4 P’s, the 5th P, which is peace of mind can be achieved. I personally believe that this is an ongoing process. One that each of us would benefit from doing at least every quarter. And as we get more and more intentional about not staying in overwhelm territory, we will become more and better at staying calm and at peace. This also offers an additional bonus by increasing our ability to observe opportunities that are present all around us, if only we were present enough to notice them.

Your First 100 Days


I was teaching a set of people principles of intrapreneurship and at the end of the class, some one came up and asked me for help. He said that he has got a new role as a product manager in his current organisation and is not sure what he can do in the first 100 days to help put him on the path of success in his new role. Here is the advice I had for him.

Be a Visionary Leader:

This works if you are being brought into the role from outside of the organisation. One reason why this is done is to infuse new ideas and vision into an already mature or a struggling product. If you know that this is the case, then you may want to play the role of a visionary leader. You need to know enough about the product and its target market so as to come up with a bold new vision for the product. You need to be ready with a clear action plan for the first 30 days, 60 days and 90 days and communicate the same with confidence.

Be a Student:

If you know that you have not been brought in to shake things up, there are two approaches (Inside-out and Outside-In)that you can take to learn about your product and the people building, marketing and selling the product.
Inside-out approach to learn:
When taking this approach, you need to try to absorb all kinds of information about the following:
  • The product: What were the core decisions that made the product what it is today? Why were they made? Who made them? How is the product sold? How is development decisions being made? And everything else (technology, architecture, marketing, branding, etc)
  • The people making the product: Who are the key stake holders? What is each one of their traits? Are they data driven or gut driven or driven by customer feedback? How open are they for change? What are their aspirations? Who works best with each of them? What can you learn from stuff that these stake holders approve about their preferences?
  • The people marketing the product: How do they market the product? Do they highlight something specific about the product? How do they find prospects? Where do they find the prospects?
  • The people who sell the product: What aspects of the product do the sales folks use to position the product? Is it consistent with the way the product is marketed/created? If not, why? What kinds of conversations do the sales teams have with the customers? How long is the typical sales cycle?
Outside-in approach to learn:
Understand everything about the customer that the product is being made for.
  • What are they using the product for?
  • What delights/irritates them about the product?
  • What is the job that the product is doing?
  • How easy is it for these customers to discover/purchase/use the product?
  • Who is your competition – not just direct competition but indirect as well (using the jobs-to-be-done framework)? Where do they find their prospects?
  • Would they miss your product if it is gone? Why?

In Conclusion:

Ideally, you would need to do all three, but the sequence in which you do them may depend on a variety of factors. How customer centric is your organisation, how open it is for change, why have you been brought in (to disrupt or to maintain the status quo), how well aligned the organisational parts are and most importantly, where your comfort level lies. While I have created this for a product manager, you could use the same checklist if you were a CEO or a business unit head to plan your first 100 days in your new role.

PBTO55: Unleashing Human Performance with Jason Forrest (@jforrestspeaker)

Credits: Opening music credit goes to Riju Mukhopadhyay & Pavan Cherukumilli

Who is on the show:

In this power packed episode, we host Jason Forrest, the CEO and the Chief Culture officer at the FPG group. As a sales professional, author, speaker, and coach, Jason’s job is to empower professionals and executives to unleash their human performance and master their leadership skills in sales, management, culture and service; for the purpose of increasing profit through people.

Why is he on the show:

He is a salesperson first, a behavior change expert, a national speaker and a coach who pushes organisations to become highly profitable while creating a “best place to work” culture. Every year, Jason delivers approximately 92 keynotes/seminars and conducts 850 group coaching calls with sales teams, managers, and executives.

What do we talk about:

In this power-packed and a free-wheeling conversation, we talk about the following:

  • What holds back people from success?
  • How can we hire people for their belief system and cultural fitment?
  • Once we hire good people, what could be done to make them succeed and get them to peak performance as quickly as possible?
  • The importance of coaching and how to transform your managers to become coaches?
  • The difference in the approach of a manager vs a coach
  • How does FPG build and maintain a high performance culture?
  • His formula for growing their top-line of any sales organisation’s performance
  • Books that had a profound impact on his thinking
  • His approach to self development
  • What he thinks is so obvious but people always miss

How can you connect with him:

You can find more information about his award winning team and coaching program at FPG. You can also connect with him on twitter @jforrestspeaker