When is it time to cut and run? Just decide that you can’t win and pack it in. If you’re going to do this, earlier is better, but when? As will all parts of your business, this should be a rational fact based decision.
Time tracking. Are you tracking your time? All your time, pre and post sale? Do you have an average number of hours you spend on sales? How close are you to exceeding that average? Now sales is an art and a skill, and cannot be completely charted. But these should be guide lines.
History should be a great teacher. You should be able to set a baseline by getting your average deal size and the average amount of effort. If all lights are green, but you just have a slow time consuming process due to a difficult customer or some other items beyond your control, by all means proceed. But if you find yourself struggling trying to make a deal fit, generally chasing big dollars, and you are eating up lots of time. Now may be the time to stop swimming upstream.
Another thing to keep in mind is your capacity. If times are lean, you may have more time and slower deals. When times are hopping, you may have less sales cycles to spend on slow deals. So as with all parts of your business, support those that are productive, and trim those that are not.
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