How do I respond to an impossible task given to me by my boss?

Question

Preface: I understand how to calculate this for past changes or generic data. This is in regards to future changes before they happen in order to justify the project.

I am leading a website redesign project that involves many small improvements (ex: improving website navigation menu UX) and future proofing (ex: migrating from jquery to vanilla JS).

I have lead similar large projects with this company which all have been wildly successful and time tested -- I have been told that past success is not enough to justify this project and that I can not incrementally progress on this project to prove it's success. I have justified the project under the logic that improving the experience for the prospected customers will lead to more sales, future proofing keeps us compatible and relevant, and improving the post sales experience is good for reviews, all of which are good for the company.

However, my boss is asking for revenue projections to justify the project to investors and she says that's easy for me to get. I asked for an example and help but she only responds that "it's easy". I've also asked our finance department for help and they told me that they can't help calculate IT.

A few challenges:

1. There are many other factors of the business which can affect the success or failure of this project (ex: if the marketing team runs an ad, it can make the website changes look awesome).
2. The release cycle does not allow for isolating changes.
3. We do not have an A/B testing system in place (actually one of the things we want to implement).
4. I need reproducible calculations that accurately predict the future so I don't lose my job if they're wrong.
5. It is my job to do this redesign, but it is also my job creating a report predicting the future. So it's not like I can just move on to another project.
6. The deadline for this report is 2 weeks.

Outro: Yes, this is a serious request from my boss and real situation. No, I don't think you guys can predict the future either. Why I post this in Workplace is because I recognize that this is a Workplace issue and not an actual solvable task that I've been assigned. Help!

Answer 1

In The Soul of a New Machine, Tracy Kidder describes a contest as to which machine Data General will build. "At a meeting [...] the two sides traded promises." In short, the managers made claim after claim of what they could build. None of those promises were based in reality. It was a form of "management poker" trying to get the other side to fold.

Management poker happens because top management operates on numbers, the accountants and financial people have control. Budgets are granted to different departments based on these promises of results. Yet, nobody really knows how much they will sell in the next week let alone the next year. Yet, sales departments have to generate numbers to satisfy the management. These numbers are, for the most part, pure fantasy. So, salespeople are given quotas and fired when they don't meet quota.

So how to play "management poker" when coming from an IT perspective? IT people have nearly zero idea of how much sales will improve because of a program change.

The best way is to become good friends with the salespeople. Find out what they believe could be done. Run all ideas past the VP of Sales and get that person's input on what value those ideas have. In short, get the salespeople to give you the numbers to justify doing the work. They are used to generating the numbers for this poker game. (It also helps a lot to have sales requesting the changes.) The other side is to put upgrading the technical debt into the pet projects of the VP of Sales. Package all sales requests with other needed bug fixes and necessary redesigns and get a single value number for the whole package. That way, both sales and IT work together to improve the systems.

It is an "art form" that we get better at through practice. But IT people are at a strong disadvantage because we are used to having to tell the uncomfortable truth, not fantasies. That is why salespeople are far better at this "poker game". Use them.

Answer 2

I think your boss is deliberately trying to make a point to you. Specifically they are trying to show you how it is that they have to think, and get you to make decisions based on more than just code.

As a coder you have proposed a web redesign which "makes many small improvements". I'm guessing a redesign is quite a costly and time-consuming thing - you are essentially rewriting a website that already functions adequately.

The question your boss has to answer to investors is "If we spend $nnn on this redesign, will that bring in more than $nnn in revenue to the company?". If it will it's worth doing. If it won't it's not.

Your boss doesn't have those figures. You are the person pushing to do this redesign, so it's really up to you to find those figures from somewhere. The point your boss may be trying to make is that if you can't get those figures then it probably isn't worth staking a whole lot of money on a redesign that may not bring in extra revenue. If your answer to him is "I can't get those figures" that is itself an answer, and means the project probably isn't worth it. Remember that you always have the option of doing incremental improvements to the website, rather than a complete redesign.

Some things you can try:

1. Talk to the people who interact with your customers - are those customers unhappy with the way the website is now?
2. Look at the effort spent in customer support of the website. Could you reduce that cost by improving the website?
3. Would the redesign give your website features your competitors don't have?
4. Look at other improvements made on the website from the past. Did they increase the number of customers using the website?
5. What does marketing think about the new website look you are proposing? Do they think they could make a good ad that would bring in many new customers?

If you can't get these figures, then you may have to admit that the changes you propose aren't worth it to the company. As an alternative you can take an approach of making the improvements you want incrementally to the existing website. You could certainly implement an A/B testing system without having to rewrite the website.

Coders love to rewrite code. But for companies it's often a bad idea, because it's very expensive; if it doesn't have a clear justification for why it should be done it's usually a bad idea.

Answer 3

So, based on the Comment - how to respond to an impossible question - there are some options:

1: Respond to a Possible question.

Politicians (of all stripes/persuasions) do this all the time - You answer the question you can answer, rather than the one you can't. So, change the parameters of the question enough so that you can answer. The key thing specific to your scenario is to consider who the target market is - it's not your Manager, it's the Investors.

2: Respond with a range of options.

So, a conservative guesstimate, a probably guesstimate and an optimistic guesstimate. You can base these on calculations, which will give them an air of authenticity e.g. "Well, if we use a start point of X, which is an industry standard/based off of similar products/based on previous experience - we should expect Y" - you can use a +/- 10 or 20% depending for your variations.

3: Respond in Email with questions about the requirements.

Essentially, her to put in writing that she's giving you an impossible task. This can be helpful if you want to go down the malicious compliance route - but sometimes getting it in writing can help because you can run it past a second set of eyes who may be able to narrow it down to something you can answer.

Answer 4

Your boss can't expect revenue predictions to be accurate; they will be based on assumptions, and it appears that your boss doesn't want to make those guesses, and has delegated the task to you.

So you need to make your best guesses about the future, and most importantly, clearly document the assumptions alongside your predictions for the future. It may help to give 2 predictions, one optimistic and one pessimistic, though your boss probably won't use the pessimistic one.

It'd really help if you could provide some financial data about previous projects to back up your predictions; you have said the finance department can't help with future estimates, but maybe they will provide some data about past projects. If you really can't get anything from them, you can mention that in your report - but be careful, you don't want to make an enemy in the finance department.

Answer 5

It's quite obvious that your justifications are not quantifiable.

A good UI will undoubtedly attract customers and a bad one will deter them, but it's impossible to assess the value of any given tweak until it is actually implemented and customer response measured (if indeed that is even possible after-the-fact).

In the meantime, you stand in the shoes of the customer, together with your trained eye, and you act on your judgment about the perceived quality of the UI and the potentials for improvement. That's the reality of what's going on.

Your project may be in serious trouble if your boss isn't willing to accept those judgments or act upon them, because there is no chance of producing genuine money figures before the work in question has completed.

Answer 6

Your boss is trying to give you the easy way out to cancel your project without losing face, because your boss can't justify the cost to her boss and your boss doesn't want to lose her job over this. So your boss is asking you to figure out what she can tell her boss when the shit inevitably hits the fan and she is asked to account for your work for the past N weeks while you've been doing this redesign.

Of course, taking existing features and rewrapping it in a new-or-different framework isn't likely to produce increased revenue for the company, and near-definitely won't do so immediately. The benefit to doing as you propose is to get your code off an old and unsupported tech stack and on to a new and better-supported tech stack to make it easier for continued development (and company continuity) and getting ahead of possible deprecations. Neither of these provide value to the company immediately, and may not provide value ever. However, the alternative to this is that, someday in the future, whatever the web-browser-du-jour is may decide to not support such archaic technology as jQuery, and suddenly nobody will be able to access your company's website. At which point your company will have to scramble to get their website back online, losing weeks or perhaps months of potential revenue. Will this happen? Who knows? When will it happen? Also, who knows? It may happen never, it may happen tomorrow. But since this is a major unknown, you can't calculate it into any value proposition that you can send to your boss (or your boss's boss).

So, the answer here, is to do your job. Your job, as far as you should be concerned, is whatever your boss tells you to do, and not whatever your boss tells you not to do, which, for now, includes this. You should document this instance, in writing, and most importantly ask your boss the following question, in writing: "Do you acknowledge that I have warned you of the potential dangers of not doing this project, and furthermore you acknowledge that you have declined my suggested course of action on the basis of lack of a company financial value proposition for doing so?" This is a CYA so that your boss can't come to you in a year from now when shit hits the fan and say "why didn't you warn us sooner of this?".

Other than that, don't engage in this course of action. This action does not provide financial value to the company, and the company doesn't engage in anything that doesn't provide immediate financial value. That's how they see it, so if the shit hits the fan and the company explodes because they didn't follow your advice, that's on them, not on you.

Answer 7

No different than any business plan. You make and state reasonable assumptions and calculate the future based on those assumptions.

“I assume the new features will result in retention of X% of customers who would otherwise leave and the acquisition of Y% more customers than currently assumed in the companies give year plan. The costs are estimated to be Z person hours.

Under these assumptions the rate of return on investment is above the company’s criteria for new projects.”