21 Questions That Matter for Businesses in 2021

Hitesh Dhawan
6 min readOct 13, 2021

In 2021, businesses have faced many problems, such as a lower physical customer base, spotty suppliers, and decreased sales.

Fortunately, digital transformation has become highly accessible for everyone.

That said, here are 21 questions that shall make you a bit uncomfortable, and help you add some exciting and meaningful tasks to your to-do lists.

Photo by Chris Montgomery on Unsplash

1. How do we add workplace flexibility and still achieve our goals?

There is a good chance that in the current scenario, your enterprise has some employees working remotely.

The key to keeping your remote staff productive and happy is to not micromanage.

Allow your remote employees to keep their own hours so long as deadlines are met.

Also, don’t forget to check in on them regularly — they miss out on the vital social connection of working with other peers.

2. Does the board understand why digital transformation is a necessity?

The aim here is to build up your board’s digital aptitude.

You don’t need them to be the next Bill Gates, but rather, the goal is for them to understand the implication of technology on the business and sources of revenue.

Take artificial intelligence, for example. It increases the efficiency of a business, often by a factor of 10. (Source: The Harvard Business Review)

3. How far should we (as a business) take digital transformation?

There’s no straight answer to this, but ideally, digitize your business as much as is possible by improving and automating workflows.

It is probably a good idea to consult an external professional if you’re unsure (they also usually offer intensive training programs for your board members on digitization).

4. Which audience is naturally attracted to us, and what do they need the most?

As with most other things related to a business, even their main customer markets have changed.

You need to reevaluate your target audience and prioritize the needs of people who are still transacting with you, even if their needs are not your main service/ product.

This is an excellent opportunity to use technology and digitization to kill two birds with one stone: outreach and CSR (corporate social responsibility).

For example, a local business that has digitally transformed into an online store may choose to offer college students a discount on their products.

For example, if your business offers a college student discount, you might choose to extend that to anyone with a valid college card (part-time, long-distance, etc.) to reach a wider community.

5. Do we need to change our business model to adapt to market changes?

When all else fails, a new business model can be your savior.

For example, a store-based business can go 100% digital and save around $800 — $ 3000 per month on rent (depending on their scale of operations).

8. How deep are we rooted in tradition?

This is probably the biggest fear that enterprises have when undergoing a technology overhaul or digital transformation.

It mainly affects creative businesses like art galleries, publications and production houses, etc.

Fear not, though — contrary to popular belief, loss of culture is almost unheard of when upgrading your tech because the tech is meant to assist your work, not replace you.

9. What steps are we taking to prioritize health?

Naturally, in current times, health is to be prioritized above all other things. To do this, most physical businesses need to implement “distancing bubbles,” regular sanitation, mandatory clinic visits, and the like.

10. What opportunities does the economic downturn present to us?

There are some upsides to the current business slump: for example, you could use this time to opt-in for professional development for the team.

11. Which of our current initiatives should we ramp up, down, or halt altogether?

This is closely related to your audience. Your business needs to prioritize those initiatives that cater to the majority of your current audience.

It doesn’t matter what your past customer base wanted — that’s all changed and gone out the window.

Give your customers what they want, and your venture will boom.

12. Where can we trim running costs?

Implementing tech-based or AI-powered solutions can cut costs to a significant degree, so you may want to look into that.

For example, AI and ML (machine learning) greatly help with inventory management and prevent deadstock.

13. Are we putting enough effort into networking?

A good yardstick is to keep your networking activities proportionate to your supply capabilities.

Don’t be enthusiastic. Don’t bite off more than you can chew.

It is also wise to maintain a portfolio on online networking sites such as LinkedIn.

14. Do we need to focus on networking or nurturing existing relations?

Let’s reference the answer to the previous question: if you ascertain that you don’t need to create new connections, work on improving relations with your existing network.

Digitization makes it much easier to keep in touch: a simple “How’ve you been” to your peer usually does the trick.

15. Do we maintain work-life balance?

Acknowledge the people who prop your business up: the employees. A productive workforce is the secret to success behind every business.

Make their lives easier by allowing remote work and digital tools like zoom and jamboard to reduce physical meetings.

16. Will a digital transformation fundamentally change how our business creates value?

The Harvard Business Review supports the claim that in most cases, an enterprise’s digital transformation aspirations are simply not bold enough to make a difference. Hence, the venture sees no active change and says digitization is a flop.

Translation: don’t be afraid to plan big and make radical changes if necessary.

17. How irreplaceable are we?

When talking about how much of a risk one should take, especially considering the scenario in 2021, we’d be remiss in not mentioning this point,

If your sector is saturated, your competition will be high. If that is the case, moderate your risks because you could get wiped out if things go south.

So maybe start an e-commerce store alongside a reduced brick-and-mortar shop instead of closing down your shop entirely. Try to find middle paths like these if you’re still hesitant to digitize.

18. How does the board gauge if their digital transformation is working?

Important note: ROI is not taken into account when gauging whether the digital transformation is working.

Instead, businesses gauge the efficiency of a digitization campaign by measuring value-tied indicators (customer fulfillment, reduced “first quote” times, in most cases, etc.).

19. Is the business using its data right?

The only way to get out of the 2020 business slump is to efficiently utilize your venture’s data as part of its operations.

An essential tool in the current business scene is predictive analysis, aided by technologies like AI and ML.

You need to ask questions like “which customers will respond best to X initiative” and “how can I boost transactions and engagement with X community.”

20. What do we want to be known for?

Unfortunately, too many people put off answering this query until it’s too late and attempt to do a “bit of everything” to serve a broader customer base.

As the saying goes, it’s a bad idea to be a jack of all trades and master of none.

21. What do we not want to be known for?

Customer opinions can change in the blink of an eye (for example, Burger king’s “women belong in the kitchen” ad cost them dearly).

Even if you don’t answer question 20 before you start, create a “no-no” list and ensure that everyone associated with your business abides by it.

Digitization of your business is the way to overcome most of 2021’s pressing issues that are currently plaguing enterprises. Let’s not delve into why digitization is necessary — we can all figure that one out.

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Hitesh Dhawan

A digital evangelist, entrepreneur, mentor, digital tranformation expert. Two decades of providing digital solutions to brands around the world.