If I was him I'd be sitting thinking the following .....
Season 1 - Came in halfway through, got a Scottish Cup Final and top 6
Season 2 - Best of the rest, despite losing some valuable squad members, brought in a couple of decent lads with Law sticking out (had worked with him before and knew he had something) and Higgy especially in the second year of his deal.
Season 3 - Best of the rest, lost a couple of key players and due to their performances and a few may also be headed elsewhere. Got the Scotland backroom job and respect from my peers in award nominations and in the press.
Season 4 - Looking to do pretty much a partial rebuild as performances over the past year in particular have ensured that a number of players can move on to make an extra cash despite enhanced offers. The club needs to sell one young asset per year to progress and remain financially viable as income from 4,500 core fans, prize money and telly only goes so far. This could involve Ojamaa or Hutch as these are our best hopes. Been out the loop in the English lower leagues for 2.5 years now, knowledge is more in Scottish game. Team at present needs 6-8 resignings/new faces/youth team promotions and stands as:
----------------- Hollis ------------------
? - Hutch - Ramsden - Hammell
? -- Lasley -- Carswell -- Lawson
---------- Ojamma ---- ? -------------
Bench
GK?
Cummins
ZFA
McHugh
?
?
?
Ambition - I'd ask myself, how will the rest of the division do next year? Will our competitors lose a number of their key players too? If so, then what are our chances of attaining top 6 again? Will that raise my stock both here and down south further? Will staying in Scotland cement my standing or do I see myself settling in an environment that everyone seems to say is a pleasure to be involved in? Do I harbour ambitions of managing at the very top level, would staying put for another few years help with that or not?
Is the grass really greener at Sheffield Utd? I wasn't given a baptism of fire at Motherwell, there was a strong core of players, covering a wide age range with a high morale level. Will I enter a similar situation of have to take two steps back (resulting in criticism from the impatient) to go one forward? I'd probably have a rebuild here too granted with greater resources.
Do I want to put my family through another move and upheaval to potentially be cut adrift in 6-12 months time if it doesn't go to plan? If so, would my stock recover (McGhee?), if so, how long will it take and will I get back into a working environment like Motherwell? Will I have burned my bridges?