Wednesday, October 14, 2020

Contractor Life - Pt 4: Making Success


This is the fourth piece looking at life as a contractor, when that isn't your
first choice of gig. The first part is here. The second can be found here.
The third is here. Please continue with me on this journey,


The question of "professional responsibility" or "responsibility" in general, is one that is hard to describe in sweeping terms. Instead, I look at it in very small, granular ideas. These grains of ideas might add up to something bigger for you. . 

First, when working, work. You can't stay 100% focused all the time. That is obvious to anyone who has ever worked in software. There are ways to do redirection which can help you maintain focus. A brisk walk to get some tea or coffee or up and down the hallway a moment. 

Working from home? A short walk away from your work area and back might do the trick. Come back ready to go.

If the client wants 10 things all at once, don't promise what cannot be done. Have the conversation around what can be done, by what point, when combined with other accountabilities for the organization and the team. 

Work to define what is really the most important of these. Then the next most important, and so on. Of course, the priorities are likely to change. The availability of resources can impact what can be worked on. Other needs might arise which need to be addressed. 

Address them. 

Also note the time and effort it took to handle the changes and how these impacted your ability to deliver on the 10 things the client originally said they wanted. 

Communicate with them. Let them know that working on issue X will impact your ability to deliver Item 1 on time. Is that what they want or should you focus on Item 1 and work on issue X as a secondary task? 

This does not mean stop and do nothing until you get direction. Work on understanding both of them. This understanding will help you structure your work so even if you are blocked on one thing, you will not be blocked on everything. 

This is pretty normal. It is not significantly different from working as an employee, right? One big difference is being able to account for what you are doing. You need to be able to show what you are working on and maximizing what you can produce. Another big difference is a basic rule, no "extra work" is done unless you can bill for it. Do not work any hours you cannot report and bill for. You are not an employee. You are an hourly worker, paid to do specific tasks, by the hour.

That is why you need to be able to show what you are doing and working on. You need to show that you can make progress on important tasks even when "blocked" on the top priority items. 

Yes, there is a cost to switch back and forth between tasks. I don't recommend it unless there is a clear reason to do so. If you are waiting for a response to a question that needs an answer before you can proceed, that might be a reasonable thing to do then. 


When it comes to "questions," odds are you'll be asking a lot of them when you start a new engagement (contractor-speak for 'gig'.)  Be open to the responses. Also, look for how the answer is presented, not just what the answer "is."

Was there a sigh or a pause before the answer? Was there some hesitation as if selecting the "right " words? These might point to areas the other person is concerned about or has some other insecurity. It might be an opportunity to offer help.

Yes, I get the "don't impose help" basic rule. This is not really "imposing help." Sometimes a little empathy and a leading question can go a long way

"You seem a little unsure about answering that. It's OK. Maybe we can come back to it. Or, is there something you'd like to talk about now?" 

Coming in from the outside, contractors can bring a fresh set of eyes to situations and problems in the organization. It might be that your experience is different from the experience of others you are working with. If most of the teams have been there a long time this is likely. If many are in their first one or two jobs in software, it is a certainty.

You can bring a perspective they do not have which can help them. 

It may not be your "job." It is one way you can help them and demonstrate how you can contribute to the project being a success. It is a small amount of effort to hear their questions and give suggestions based on your experience and understanding of their situation. 

By building a relationship based on trust, you help them do their jobs better. You help address the questions they have and present them in ways they could not present them. 


Building trust is the most obvious and easiest way there is to bring value to your clients. When the people you work with come to you asking for suggestions or advice, it often means that they and the rest of the team have never encountered the situation before and need guidance. It is highly probable their leadership has likewise not encountered the situation. If they had, it seems unlikely the team would be coming to you if their leadership had already given them advice or direction.

There is one more really important factor to consider. 

Always be honest. As tempting as it is to say what the client wants to hear, if that is not true or accurate, don't say it. Be forthright. If something they want to do seems a bad idea, say so. Tell them it is a bad idea, and why. Offer a suggestion or an alternative direction.

If there are multiple "outside" agencies involved, be aware of their motives. Are they operating in a boiler-plate approach? Where one-size-fits-all? Are are they working to meet and fill the unique needs of THIS client? If there is a large team from one or more organizations, are they operating in a way that makes sense?

If their performance measures for their teams and individuals are not in alignment, tread carefully. Watch to observe behaviors of individual contributors and how they differ from the client's employees and those of the other agencies.

In this thing, one key point to keep in mind: going with the flow from the predominant agency may not be in the best interests of your client. 

Always act with your client's best interests in mind. Be willing to explain your perspective and reasons for the differences. Let them decide, then act accordingly.

Making Success

The great challenge for most people appears to be not having a tangible idea of what success is, or looks like. For some, it is a large income with a fancy title, the ability to afford a really nice car and home. The ability to join the "better sorts" of society.

That might work for some. I find the idea of success to be illusory. What others bestow on you, they can also take away. What you can do for yourself, your family and friends is more real. I find "success" to be paired with "happiness."

There is a quote often attributed to Mary Kay Ash, the founder of the cosmetics company which bears her name, Mary Kay. It runs:

"Happiness is having something that you love to do, someone to
love, and something to look forward to."

For software professionals, I believe this translates to something like, "interesting work solving interesting problems, someone or something to care about other than yourself and something that can be achieved to reward yourself with."

I cannot define what success looks like for you or anyone else. I cannot tell you what motivates you. I can tell you my thoughts on the idea of success no matter if it is as an employee, contractor or consultant. Maybe there will be something there to help you find your idea of success. Maybe that will help you find what motivates you to reach it.

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