We’re displeased with this employee for a number of reasons. We contracted him through Upwork three months ago (he had pretty good reviews) to build a data dashboard for us.
We gave him very specific due dates for certain segments of the product and numerous projects are coming in late.
He also has charged us double the hours that he quoted us for a number of the segments.
So we’re now past-due on this and over-budget, but I can’t cut him loose because we’re too far along and I worry that grabbing his work and giving it to another programmer will just cause more delays to get that person up to speed.
How can I encourage this individual to get things moving?
I think you are misdiagnosing an motivation problem that is actually an ability problem.
You say you this person (who you found on Upwork) specific due dates. I am guessing that because you just found them on Upwork, you don't have enough past history to know whether those dates are realistic for them or not. The dates and effort estimates you made might be realistic for someone else -- yet maybe this person you hired works slower than they other people you know.
This might have been avoidable if instead of them due dates you had them to tell you when they will complete the work. That's generally more advisable in general, but especially when you are working with someone whose skills and productivity you have no experience with. But you didn't do that, and can't change the past, so let's just move on.
It would have been good if the contractor had said at the time "I can't meet those dates". Then you might have sought for someone else more skilled.
Unfortunately, many employees and contractors don't do that. Some don't do that because they overestimate their own capabilities, just as you overestimated your ability to choose a person who would complete the work on time and within budget.
Others don't tell you how impossible your requirements are deliberately, because they are sure you will just give the work to someone else, and they are used to securing the contract first and then working out the cost overruns and delays with the client who feels boxed in, just as you do.
Sometimes there are also cultural expectations. In some cultures it is impolite to tell the customer they are wrong or can't have what they want. It is more polite to di the best you can and apologize. That could be the problem too.
If you are correct and this is just a motivation problem you can offer them a bonus for every day earlier they complete the work. But you might risk getting something quickly that isn't well tested, or that they may take shortcuts that will undermine reliability. So be careful what you wish for and make sure your incentives are perfectly aligned with what you need.
However, if the underlying problem really is an ability problem, incentives won't help, and penalties for failure will make their stress later your situation worse. In that case, you need to go back to the contractor and find out what the ability problem is and offer to help them solve it.
Many taxpayers want contractors for big ticket infrastructure projects like a bridge to be charged penalties for every day they are late in completing the work. The problem is once the contractor finds out that the project is harder than budgeted or will be late, they might walk away once they start losing money. So instead, they are often offered extra profit for authorizing more overtime in hopes of limiting delays.
You might be in the same boat. Ask your contractor if they know someone who could help them complete the work sooner, and offer to pay for it.
Otherwise, take your loss, find a new replacement and be more realistic in letting them estimate delivery time.
Always make payments contingent on results. That means quality of work and deadlines met.
Hopefully, you haven't paid all in advance, so it may not be too late to "lay down the law".
Depending on the particular contract you signed, you might be able to re-negotiate, to pay any remaining amount, based on milestones met.
Before you do anything, however, make sure you have the latest version of the source code, just in case you need to fire the engineer.
This is why a technical co-founder is absolutely critical. You need someone who can see through any "BS", and keep things under check.
Outside contractors, or even employees will never have the same kind of dedication as an owner / founder of a business.
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